Diallyl Disulfide

Diallyl Disulfide at a Glance

Diallyl disulfide (DADS) is the lipid-soluble sulfur compound that gives steam-distilled garlic oil most of its smell and most of its pharmacology. Two allyl groups joined by a two-sulfur bridge, it sits in the middle of a family — diallyl sulfide has one sulfur, DADS has two, diallyl trisulfide has three — and, as argued above, that sulfur count is the single most useful thing to know about the whole group.

The molecule’s most important quirk is that it is barely present in garlic itself. Intact cloves store alliin; crushing converts it to allicin; allicin then falls apart, and DADS is one of the pieces. In practice the diallyl sulfides show up in quantity only when garlic is distilled or heated — HPLC of commercial garlic products found the diallyl sulfide series to be the exclusive sulfur constituents of steam-distilled garlic oils, and absent from garlic powder, gels and aged aqueous-alcohol extracts ^{12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →}.

Its documented thread is phase II enzyme induction: fed to rats, DADS raises glutathione S-transferase, quinone reductase, epoxide hydrolase and UDP-glucuronosyltransferase across liver, gut, kidney and lung, and blocks the mutagenicity of several ultimate carcinogens in parallel ^{4,5Reference 4Guyonnet D et al. · 2001Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme inductionView study →Reference 5Guyonnet D et al. · 1999AnimalModulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissuesView study →}. That is the mechanism usually offered to explain why populations eating more garlic report less gastric cancer ^{1Reference 1Kodali RT · 2015Meta-analysisMeta-analysis: does garlic intake reduce risk of gastric cancer? Nutrition and Cancer. https://pubmed.ncbi.nlm.nih.gov/25411831/View study →}. It is a good mechanism. It is also, so far, a mechanism without an isolate trial behind it — the honest version of that story is set out below.

A Distillation Product, Not a Clove Constituent

The garlic literature routinely lists DADS as a “garlic constituent” alongside alliin, allicin and S-allylcysteine ^{31Reference 31Shang A et al. · 2019Bioactive compounds and biological functions of garlic (Allium sativum L.)View study →}. That is true only with a large asterisk, and the asterisk matters for how you read every study here.

Garlic’s stored sulfur is the odourless amino-acid derivative alliin. Damage to the clove releases alliinase, which converts alliin to allicin within about 20 seconds at body temperature ^{13Reference 13Lawson LD · 1992Characterization of the formation of allicin and other thiosulfinates from garlicView study →}. Allicin is unstable, and its decomposition products depend entirely on what happens next:

What is done to the clove	Dominant sulfur products	DADS present?
Left intact	Alliin, methiin, isoalliin (no thiosulfinates)	No
Crushed, eaten raw	Allicin and other thiosulfinates	Trace at most
Macerated in vegetable oil	Vinyldithiins and ajoene	Minor
Steam-distilled	Diallyl mono-, di-, tri- and higher sulfides	Yes — the main products
Aged in aqueous alcohol	S-allylcysteine, water-soluble derivatives	No

Lawson’s 1991 HPLC survey of commercial garlic products is the cleanest statement of this: thiosulfinates were released only from cloves and garlic powder; the vinyldithiins and ajoenes appeared only in oil-macerates; and the diallyl, methyl-allyl and dimethyl sulfide series were the exclusive constituents of steam-distilled garlic oil products ^{12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →}.

So is DADS an artefact? Partly — and it is worth being precise about which part. The molecule is a genuine thermal/oxidative decomposition product of allicin, so it forms whenever garlic is cooked, distilled or left to break down, and it is unambiguously a real constituent of garlic oil, a real food ingredient people really consume. What it is not is a compound the living plant makes and stores. Any claim of the form “garlic contains DADS, therefore garlic does X” has skipped a processing step. Conversely, an assay run on fresh crushed garlic is testing allicin, not DADS — which is why, for instance, the bacteriostatic activity of garlic extracts against Helicobacter pylori tracks the thiosulfinates, not the sulfides ^{27Reference 27Cañizares P et al. · 2004Allyl-thiosulfinates, the bacteriostatic compounds of garlic against Helicobacter pyloriView study →}.

The Polysulfide Chain-Length Gradient

If you only remember one structural fact about garlic’s oil-soluble sulfides, make it this: activity scales with the number of sulfur atoms in the bridge, in the same direction for benefit and for harm.

The chemistry behind it is straightforward. A polysulfide chain is a weak point. Attacked by a thiol — glutathione, a cysteine residue on a protein — it cleaves, and the more sulfurs there are in the chain, the more readily it does so and the more sulfur is released as hydrogen sulfide (H₂S) or as reactive perthiol intermediates. Benavides and colleagues showed this directly: human red blood cells convert garlic polysulfides to H₂S, and the yield rises both with an allyl substituent and with increasing numbers of tethering sulfur atoms, with vasorelaxation of aortic rings tracking the H₂S output ^{15Reference 15Benavides GA et al. · 2007Hydrogen sulfide mediates the vasoactivity of garlicView study →}.

Compound	Sulfurs	H₂S donation	Phase II induction (rat)	Haemolytic/oxidant	Antiplatelet (in vitro)
Diallyl sulfide (DAS)	1	Negligible	Weak 2Reference 2Munday R · 2001AnimalRelative activities of organosulfur compounds derived from onions and garlic in increasing tissue activities of quinone reductase and glutathione transferase in rat tissuesView study →	Not significant 3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →	Weakest of the three 16Reference 16Chan KC et al. · 2002Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregationView study →
Diallyl disulfide (DADS)	2	Moderate	Potent 2,4,5Reference 2Munday R · 2001AnimalRelative activities of organosulfur compounds derived from onions and garlic in increasing tissue activities of quinone reductase and glutathione transferase in rat tissuesView study →Reference 4Guyonnet D et al. · 2001Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme inductionView study →Reference 5Guyonnet D et al. · 1999AnimalModulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissuesView study →	Moderate 3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →	Intermediate 16Reference 16Chan KC et al. · 2002Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregationView study →
Diallyl trisulfide (DATS)	3	High	Potent 2Reference 2Munday R · 2001AnimalRelative activities of organosulfur compounds derived from onions and garlic in increasing tissue activities of quinone reductase and glutathione transferase in rat tissuesView study →	Strong 3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →	Strongest 16Reference 16Chan KC et al. · 2002Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregationView study →
Diallyl tetrasulfide	4	Highest	—	Strongest 3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →	—

Munday’s comparative rat study is the load-bearing citation and the most honest one, because it measured benefit and harm in the same animals. Monosulfides did essentially nothing on any endpoint. Di-, tri- and tetrasulfides all generated hydrogen peroxide in the presence of glutathione and haemoglobin and damaged erythrocytes, with potency rising tetra- > tri- > di-; in vivo, tri- and tetrasulfides were powerful haemolytic agents. But only the allyl compounds raised quinone reductase and glutathione S-transferase — the propyl analogues from onion were completely inert on that axis ^{3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →}. A separate dosing study ranked diallyl trisulfide and diallyl disulfide as potent phase II inducers and diallyl sulfide as weak ^{2Reference 2Munday R · 2001AnimalRelative activities of organosulfur compounds derived from onions and garlic in increasing tissue activities of quinone reductase and glutathione transferase in rat tissuesView study →}.

Where DADS sits. Two sulfurs is enough to be a strong phase II inducer but not enough to be a strong oxidant. In every side-by-side comparison available, the trisulfide is the more ready H₂S donor ^{15Reference 15Benavides GA et al. · 2007Hydrogen sulfide mediates the vasoactivity of garlicView study →}, the stronger platelet inhibitor ^{16Reference 16Chan KC et al. · 2002Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregationView study →}, the more effective antifungal ^{33Reference 33Gong X et al. · 2021Diallyl trisulfide, the antifungal component of garlic essential oil and the bioactivity of its nanoemulsions formed by spontaneous emulsificationView study →} — and also the more haemolytic ^{3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →}. DADS is the middle of the gradient, and its comparative appeal is that it holds most of the detox-enzyme signal at a lower oxidant cost. Whether that trade-off means anything at human exposures is untested.

What It's Used For

Almost everything below is cell-line or rodent work on the isolated molecule. Where a human study exists, it tested a garlic preparation, not DADS.

Evidence by IndicationStrength of support · Beta

Support is an experimental score — weighted by study type (human > animal > in vitro) and volume. A beta, not a validated metric. Every score here is capped by the same limitation: no application has been tested as an isolate in humans, so read the per-row basis rather than the number.

01Phase II Detox-Enzyme InductionShaky44%Consistent multi-tissue rat induction + matched antimutagenicity ^{3,4,5,7Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →Reference 4Guyonnet D et al. · 2001Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme inductionView study →Reference 5Guyonnet D et al. · 1999AnimalModulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissuesView study →Reference 7Tsai CW et al. · 2007Diallyl disulfide and diallyl trisulfide up-regulate the expression of the pi class of glutathione S-transferase via an AP-1-dependent pathwayView study →}

02Anticancer Activity in Cells and RodentsShaky32%Two rodent carcinogenesis models + defined cell-line mechanisms ^{17,18,19,20Reference 17Reddy BS et al. · 1993Chemoprevention of colon carcinogenesis by organosulfur compoundsView study →Reference 18Suzui N et al. · 1997AnimalInhibitory effects of diallyl disulfide or aspirin on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced mammary carcinogenesis in ratsView study →Reference 19Druesne N et al. · 2004Diallyl disulfide (DADS) increases histone acetylation and p21(waf1/cip1) expression in human colon tumor cell linesView study →Reference 20Sundaram SG · 1996Diallyl disulfide inhibits the proliferation of human tumor cells in cultureView study →}

03Antimicrobial and AntifungalShaky24%In-vitro only; garlic-oil assays where the allyl group is the requirement ^{23,32Reference 23Casella S et al. · 2013In vitroThe role of diallyl sulfides and dipropyl sulfides in the in vitro antimicrobial activity of the essential oil of garlic, Allium sativum L., and leek, Allium porrum LView study →Reference 32Bhatwalkar SB et al. · 2021Antibacterial properties of organosulfur compounds of garlic (Allium sativum)View study →}

04Antiplatelet and Vasoactive EffectsShaky22%Isolated human platelets + aortic-ring H₂S work; DATS outperforms DADS ^{15,16Reference 15Benavides GA et al. · 2007Hydrogen sulfide mediates the vasoactivity of garlicView study →Reference 16Chan KC et al. · 2002Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregationView study →}

05Anti-Inflammatory and Airway EffectsShaky18%One mouse asthma model + macrophage line, Nrf2/HO-1 and NF-κB ^{30Reference 30Shin IS et al. · 2013Diallyl-disulfide, an organosulfur compound of garlic, attenuates airway inflammation via activation of the Nrf-2/HO-1 pathway and NF-kappaB suppressionView study →}

Mechanisms

The two rows to hold onto are the pi-class GST induction — pleiotropic, multi-tissue, dose-responsive, and the reason DADS was ever proposed as a chemopreventive — and the CYP2E1 down-regulation, which is simultaneously the most attractive chemoprevention mechanism and the most concrete drug-interaction risk on the page ^{4,5,6Reference 4Guyonnet D et al. · 2001Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme inductionView study →Reference 5Guyonnet D et al. · 1999AnimalModulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissuesView study →Reference 6Siess MH et al. · 1997AnimalModification of hepatic drug-metabolizing enzymes in rats treated with alkyl sulfidesView study →}.

Pharmacokinetics

DADS is small, lipophilic and metabolised fast. In an isolated perfused rat liver its half-life was 6.09 minutes with a clearance of 34.22 mL/min ^{9Reference 9Germain E et al. · 2003AnimalHepatic metabolism of diallyl disulphide in rat and manView study →}. Its principal oxidative fate is counter-intuitive: human liver microsomes convert DADS back to allicin (diallyl thiosulfinate) as the only detected oxidation product, with CYP2E1 showing the highest affinity and flavin-containing monooxygenases contributing a minority share (Km 0.61 mM) ^{8Reference 8Teyssier C et al. · 1999Metabolism of diallyl disulfide by human liver microsomal cytochromes P-450 and flavin-containing monooxygenasesView study →}; rat liver reproduces this with CYP2B1/2 and CYP2E1 as the active isoforms ^{9Reference 9Germain E et al. · 2003AnimalHepatic metabolism of diallyl disulphide in rat and manView study →}. In parallel, DADS is reduced and conjugated to allyl mercaptan and allyl glutathione sulfide — and the thiosulfinate reacts non-enzymatically with glutathione to give the same conjugate — then methylated onward to allyl methyl sulfide, which is slowly oxidised to the sulfoxide and sulfone ^{9Reference 9Germain E et al. · 2003AnimalHepatic metabolism of diallyl disulphide in rat and manView study →}. Because allyl mercaptan is a roughly three-fold more potent HDAC inhibitor than DADS itself ^{19Reference 19Druesne N et al. · 2004Diallyl disulfide (DADS) increases histone acetylation and p21(waf1/cip1) expression in human colon tumor cell linesView study →}, the metabolites are not merely disposal products; some of the parent molecule’s apparent activity may belong to them. No human oral bioavailability figure for DADS has been established, which is the central caveat for every µM in-vitro concentration cited here.

Clinical Trials

There are no clinical trials of isolated diallyl disulfide. The closest human evidence is the Shandong Intervention Trial, in which 3,365 residents of a high-risk Chinese county took garlic extract and oil (a preparation containing the diallyl sulfides) or placebo for 7.3 years: at 14.7 years garlic treatment produced only non-significant reductions in gastric cancer incidence and mortality ^{29Reference 29Ma JL et al. · 2012Fifteen-year effects of Helicobacter pylori, garlic, and vitamin treatments on gastric cancer incidence and mortalityView study →}, and at 22 years incidence was still not significantly reduced (OR 0.81, 95% CI 0.57–1.13) although gastric-cancer mortality was (HR 0.66, 95% CI 0.43–1.00) ^{28Reference 28Li WQ et al. · 2019RCTEffects of Helicobacter pylori treatment and vitamin and garlic supplementation on gastric cancer incidence and mortality: follow-up of a randomized intervention trialView study →}.

Last checked: July 2026.

The Gastric-Cancer Chain of Inference

This is the claim DADS is usually recruited to support, and it is worth laying out as a chain so the weak link is visible.

Link 1 — the epidemiology (food level). A meta-analysis of 14 case-control studies, two randomised studies and one cohort — 8,621 cases and 14,889 controls — found garlic intake associated with reduced gastric cancer risk: OR 0.49 (95% CI 0.38–0.62) for high intake, 0.75 (0.58–0.97) for low intake ^{1Reference 1Kodali RT · 2015Meta-analysisMeta-analysis: does garlic intake reduce risk of gastric cancer? Nutrition and Cancer. https://pubmed.ncbi.nlm.nih.gov/25411831/View study →}. This is an association between a food and an outcome, with the usual case-control vulnerabilities: recall bias, wide variation in how intake was defined, and confounding by an overall vegetable-rich diet. The authors say plainly that further high-quality studies are needed and that the protective amount is unknown ^{1Reference 1Kodali RT · 2015Meta-analysisMeta-analysis: does garlic intake reduce risk of gastric cancer? Nutrition and Cancer. https://pubmed.ncbi.nlm.nih.gov/25411831/View study →}.

Link 2 — the mechanism (cell and animal level). Garlic’s allyl sulfides induce phase II carcinogen-detoxification enzymes; DADS does so more comprehensively than its relatives, and does so in the gastrointestinal tissues where the epidemiology points ^{4,5Reference 4Guyonnet D et al. · 2001Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme inductionView study →Reference 5Guyonnet D et al. · 1999AnimalModulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissuesView study →}. It also lowers CYP2E1, the enzyme that activates nitrosamines — the carcinogen class most implicated in gastric cancer ^{6Reference 6Siess MH et al. · 1997AnimalModification of hepatic drug-metabolizing enzymes in rats treated with alkyl sulfidesView study →}. In rats, dietary DADS demonstrably reduces chemically induced colon and mammary tumours ^{17,18Reference 17Reddy BS et al. · 1993Chemoprevention of colon carcinogenesis by organosulfur compoundsView study →Reference 18Suzui N et al. · 1997AnimalInhibitory effects of diallyl disulfide or aspirin on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced mammary carcinogenesis in ratsView study →}.

Link 3 — the bridge. There isn’t one. No trial has given people DADS, or a product standardised to DADS, and measured either a detox-enzyme endpoint or a cancer endpoint. The nearest attempt — 7.3 years of garlic extract and oil in a high-risk population — did not significantly reduce gastric cancer incidence at 15 or 22 years, though gastric-cancer mortality was lower in the garlic arm at the longest follow-up ^{28,29Reference 28Li WQ et al. · 2019RCTEffects of Helicobacter pylori treatment and vitamin and garlic supplementation on gastric cancer incidence and mortality: follow-up of a randomized intervention trialView study →Reference 29Ma JL et al. · 2012Fifteen-year effects of Helicobacter pylori, garlic, and vitamin treatments on gastric cancer incidence and mortalityView study →}. Meanwhile Helicobacter pylori eradication, tested in the same trial, cut incidence roughly in half and held that effect for 22 years ^{28Reference 28Li WQ et al. · 2019RCTEffects of Helicobacter pylori treatment and vitamin and garlic supplementation on gastric cancer incidence and mortality: follow-up of a randomized intervention trialView study →}.

How to read it. The mechanism is real and reproducible; the epidemiology is real and reasonably consistent; the inference joining them is not tested. It is also worth noting that the compounds isolated as garlic’s bacteriostatic principle against H. pylori were the thiosulfinates, not the sulfides ^{27Reference 27Cañizares P et al. · 2004Allyl-thiosulfinates, the bacteriostatic compounds of garlic against Helicobacter pyloriView study →} — so even within garlic, the molecule best placed to explain a gastric benefit may not be this one.

Garlic Breath & the Allyl Methyl Sulfide Trail

Garlic breath is a two-stage phenomenon, and DADS metabolism is the second stage.

Immediately after eating garlic, the mouth carries high concentrations of methanethiol and allyl mercaptan with smaller amounts of allyl methyl sulfide, allyl methyl disulfide and diallyl disulfide — and all of these except allyl methyl sulfide are far more concentrated in mouth air than in alveolar air, meaning they are oral in origin and will fade with brushing ^{10Reference 10Suarez F et al. · 1999Differentiation of mouth versus gut as site of origin of odoriferous breath gases after garlic ingestionView study →}. Allyl methyl sulfide (AMS) is the exception. Its partial pressures are similar in mouth air, alveolar air and urine, marking it as systemic — absorbed from the gut, and uniquely resistant to gut and hepatic metabolism where its relatives are cleared quickly. After about three hours it is the predominant breath sulfur gas ^{10Reference 10Suarez F et al. · 1999Differentiation of mouth versus gut as site of origin of odoriferous breath gases after garlic ingestionView study →}. That is why garlic breath outlasts toothpaste.

AMS is a downstream metabolite of the allyl sulfides: DADS is reduced to allyl mercaptan, methylated to AMS, and slowly oxidised onward to allyl methyl sulfoxide and allyl methyl sulfone ^{9Reference 9Germain E et al. · 2003AnimalHepatic metabolism of diallyl disulphide in rat and manView study →}. All three appear in human urine, peaking about 1–2 hours after a garlic meal with a second rise at 6–8 hours in some people and up to ten-fold variation between individuals ^{11Reference 11Scheffler L et al. · 2019Quantification of volatile metabolites derived from garlic (Allium sativum) in human urineView study →}. Breath AMS is reliable enough to be used as the bioavailability marker for allyl thiosulfinates in garlic clinical trials ^{14Reference 14Lawson LD · 2005Clinical trialComposition, stability, and bioavailability of garlic products used in a clinical trialView study →}.

Isolate vs. Plant Studies

The split here is unusually clean, and unusually unhelpful.

Everything mechanistic is isolate work. The phase II induction, the antimutagenicity, the HDAC inhibition, the tumour-cell growth arrest, the antiplatelet ranking, the airway model — all used purified DADS in defined rat gavage doses, dietary ppm levels or micromolar cell concentrations ^{4,5,7,16,17,18,19,20,30Reference 4Guyonnet D et al. · 2001Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme inductionView study →Reference 5Guyonnet D et al. · 1999AnimalModulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissuesView study →Reference 7Tsai CW et al. · 2007Diallyl disulfide and diallyl trisulfide up-regulate the expression of the pi class of glutathione S-transferase via an AP-1-dependent pathwayView study →Reference 16Chan KC et al. · 2002Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregationView study →Reference 17Reddy BS et al. · 1993Chemoprevention of colon carcinogenesis by organosulfur compoundsView study →Reference 18Suzui N et al. · 1997AnimalInhibitory effects of diallyl disulfide or aspirin on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced mammary carcinogenesis in ratsView study →Reference 19Druesne N et al. · 2004Diallyl disulfide (DADS) increases histone acetylation and p21(waf1/cip1) expression in human colon tumor cell linesView study →Reference 20Sundaram SG · 1996Diallyl disulfide inhibits the proliferation of human tumor cells in cultureView study →Reference 30Shin IS et al. · 2013Diallyl-disulfide, an organosulfur compound of garlic, attenuates airway inflammation via activation of the Nrf-2/HO-1 pathway and NF-kappaB suppressionView study →}. That is a genuine strength: nobody is inferring DADS’s effects from a whole extract.

Everything human is preparation work. The gastric-cancer meta-analysis measured garlic consumption ^{1Reference 1Kodali RT · 2015Meta-analysisMeta-analysis: does garlic intake reduce risk of gastric cancer? Nutrition and Cancer. https://pubmed.ncbi.nlm.nih.gov/25411831/View study →}; the Shandong trial dosed garlic extract and oil ^{28,29Reference 28Li WQ et al. · 2019RCTEffects of Helicobacter pylori treatment and vitamin and garlic supplementation on gastric cancer incidence and mortality: follow-up of a randomized intervention trialView study →Reference 29Ma JL et al. · 2012Fifteen-year effects of Helicobacter pylori, garlic, and vitamin treatments on gastric cancer incidence and mortalityView study →}; the bioavailability and composition studies characterised products ^{12,14Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →Reference 14Lawson LD · 2005Clinical trialComposition, stability, and bioavailability of garlic products used in a clinical trialView study →}. None isolated the molecule.

And the two literatures do not share a vehicle. The isolate studies use DADS as it exists in distilled oil; most human garlic intake is raw or cooked cloves, where the dominant reactive chemistry is allicin and the thiosulfinates ^{12,13Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →Reference 13Lawson LD · 1992Characterization of the formation of allicin and other thiosulfinates from garlicView study →}. Even the DADS content of the products that do contain it varies enormously — Lawson found a 33-fold range between brands of steam-distilled garlic oil ^{12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →}. Transferring a rodent DADS result onto a garlic-eating human therefore crosses two gaps at once: species and preparation.

Prevalence in Nature

DADS is an Allium-and-relatives molecule, and within that group it is a processing molecule. It is not stored by the living plant; it appears when alliinase-generated thiosulfinates decompose under heat, distillation or time ^{12,13Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →Reference 13Lawson LD · 1992Characterization of the formation of allicin and other thiosulfinates from garlicView study →}.

In steam-distilled garlic essential oil it is consistently the second most abundant compound after diallyl trisulfide. A GC-MS profile of a Peruvian garlic accession put diallyl trisulfide at 44.2% and DADS at 22.1%, followed by allyl methyl trisulfide (9.7%) and the vinyldithiins (4.8%) ^{24Reference 24Herrera-Calderon O et al. · 2021In vitroChemical constituents, in vitro antioxidant activity and in silico study on NADPH oxidase of Allium sativum L. (garlic) essential oilView study →}. Two Egyptian cultivars gave 45.8%/15.6% and 58.5%/22.4% for the trisulfide/disulfide pair, showing that cultivar alone moves the ratio substantially ^{25Reference 25El-Sayed HS et al. · 2017Chemical composition and antimicrobial activity of garlic essential oils evaluated in organic solvent, emulsifying, and self-microemulsifying water based delivery systemsView study →}, and a Chinese oil ran 39.8% trisulfide to 32.9% DADS with 7.0% diallyl sulfide ^{33Reference 33Gong X et al. · 2021Diallyl trisulfide, the antifungal component of garlic essential oil and the bioactivity of its nanoemulsions formed by spontaneous emulsificationView study →}. Across these analyses DADS lands somewhere between about a sixth and a third of the oil — always second, never absent.

Outside garlic, the strongest reported source is Chinese chive (Allium tuberosum): hydrodistilled root oil contained allyl methyl trisulfide 35.2%, DADS 28.3%, diallyl trisulfide 20.9% and dimethyl trisulfide 12.3% — a higher DADS fraction than garlic oil itself ^{26Reference 26Liu XC et al. · 2015Laboratory evaluation of larvicidal activity of the essential oil of Allium tuberosum roots and its selected major constituent compounds against Aedes albopictusView study →}. It also occurs in wild garlic / ramsons (Allium ursinum) and in the broader Allium volatile literature.

A useful negative: onion and leek do not supply it. Their sulfur amino acids carry propyl and propenyl rather than allyl groups, so their oils yield dipropyl and dipropenyl sulfides — chemically parallel but pharmacologically distinct, inert as phase II inducers and, in leek oil, inactive as antimicrobials ^{3,23Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →Reference 23Casella S et al. · 2013In vitroThe role of diallyl sulfides and dipropyl sulfides in the in vitro antimicrobial activity of the essential oil of garlic, Allium sativum L., and leek, Allium porrum LView study →}. This is why DADS is a garlic marker and not an Allium marker.

Major Natural Sources

Source	Part / preparation	Diallyl disulfide	Notes
Garlic (Allium sativum)	Steam-distilled essential oil	15.6–32.9% of oil	Second to diallyl trisulfide; cultivar- and origin-dependent 24,25,33Reference 24Herrera-Calderon O et al. · 2021In vitroChemical constituents, in vitro antioxidant activity and in silico study on NADPH oxidase of Allium sativum L. (garlic) essential oilView study →Reference 25El-Sayed HS et al. · 2017Chemical composition and antimicrobial activity of garlic essential oils evaluated in organic solvent, emulsifying, and self-microemulsifying water based delivery systemsView study →Reference 33Gong X et al. · 2021Diallyl trisulfide, the antifungal component of garlic essential oil and the bioactivity of its nanoemulsions formed by spontaneous emulsificationView study →
Garlic (Allium sativum)	Fresh clove, intact or crushed	Trace / none	Chemistry is alliin → allicin; sulfides form on heating 12,13Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →Reference 13Lawson LD · 1992Characterization of the formation of allicin and other thiosulfinates from garlicView study →
Garlic (Allium sativum)	Oil-macerate, garlic powder, aged extract	Absent or minor	Vinyldithiins/ajoene, thiosulfinates and S-allylcysteine respectively 12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →
Chinese chive (Allium tuberosum)	Root essential oil	28.3% of oil	Highest reported single figure 26Reference 26Liu XC et al. · 2015Laboratory evaluation of larvicidal activity of the essential oil of Allium tuberosum roots and its selected major constituent compounds against Aedes albopictusView study →
Wild garlic (Allium ursinum)	Bulb / leaf volatiles	Reported, unquantified here	Same alliin–alliinase chemistry
Onion, leek (Allium cepa, A. porrum)	Bulb / stem oil	Absent	Propyl and propenyl sulfides instead 3,23Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →Reference 23Casella S et al. · 2013In vitroThe role of diallyl sulfides and dipropyl sulfides in the in vitro antimicrobial activity of the essential oil of garlic, Allium sativum L., and leek, Allium porrum LView study →

Use as a Flavouring

DADS is a commercial flavour compound, and this is quantitatively the way most people meet it. It is the backbone of “garlic” aroma in savoury seasonings, snack coatings, processed meats and sauces, and it is routinely described in the food-science literature as a major organosulfur of garlic oil “widely used as a flavoring agent” ^{30Reference 30Shin IS et al. · 2013Diallyl-disulfide, an organosulfur compound of garlic, attenuates airway inflammation via activation of the Nrf-2/HO-1 pathway and NF-kappaB suppressionView study →}. Steam-distilled garlic oil — the concentrate in which DADS is a fifth of the mass — is itself sold both as a flavour ingredient and as a dietary supplement, which is why the same molecule appears simultaneously in a spice rack and in a chemoprevention paper.

Two practical consequences follow. First, culinary exposure is small and irregular: garlic oil is used at fractions of a percent, and the diallyl-sulfide content of commercial oils varies by more than an order of magnitude between products ^{12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →}. Second, occupational exposure is not small — food handlers, chefs and garlic processors get repeated skin contact with concentrated material, which is the setting in which DADS’s contact allergenicity actually matters (see below).

Discovery & Synthesis

DADS emerged from the first chemical interrogation of garlic. Wertheim’s 1844 study of garlic oil (Untersuchung des Knoblauchöls) isolated the sulfur compounds of the distillate and named their hydrocarbon fragment allyl, after Allium — the etymology every allyl compound since has inherited ^{35Reference 35Wertheim T · 1844Untersuchung des KnoblauchölsView study →}. Nearly half a century later, F. W. Semmler’s 1892 analysis of the essential oil of Allium sativum established the diallyl sulfide series as garlic oil’s principal constituents ^{36Reference 36Semmler FW · 1892Semmler FW (1892). Über das ätherische Öl des Knoblauchs (Allium sativum). Archiv der Pharmazie. https://doi.org/10.1002/ardp.18922300603View study →}. Both were working on the distillate, which is precisely why the sulfides — rather than allicin, characterised only in 1944 — were garlic’s first known “active” compounds.

The modern analytical picture arrived with HPLC: Lawson’s 1991 survey quantified the diallyl, methyl-allyl and dimethyl mono- through hexasulfides, the vinyldithiins and both ajoene isomers across commercial products, and showed which preparation yields which compound ^{12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →}.

Synthesis is trivial and long-established — DADS is made industrially by reacting allyl halides or allyl mercaptan with sulfur donors (for example, allyl chloride with sodium disulfide), and it is sold as a bulk flavour and research chemical. Manufacture today is therefore split: flavour- and research-grade DADS is synthetic; the DADS people actually consume comes from steam distillation of garlic, where it is a decomposition product rather than an extraction target.

Patents: not yet researched.

Toxicity & Safety

DADS carries a moderate flag. That is deliberately higher than the “it’s just garlic” intuition, and it rests on three specific, documented properties of the isolated molecule — none of which describes eating a clove of garlic.

Contact & Photocontact Allergy

This is the best-documented human hazard. In the classic study, guinea pigs sensitised to garlic extract cross-reacted to diallyl disulfide and vice versa, and garlic-sensitive patients patch-tested positive to diallyl disulfide, allyl propyl disulfide, allyl mercaptan and allicin — identifying DADS as a principal garlic allergen ^{21Reference 21Papageorgiou C et al. · 1983Allergic contact dermatitis to garlic (Allium sativum L.)View study →}. It is an established cause of hand dermatitis in cooks and food handlers, has its own case literature ^{34Reference 34Fernández-Vozmediano JM et al. · 2000Allergic contact dermatitis from diallyl disulfideView study →}, appears in patch-test series as a defined allergen ^{22Reference 22Bordel-Gómez MT · 2008Sensitivity to diallyl disulfide in a Spanish populationView study →}, and has been reported as a photocontact allergen as well. Gloves are the standard occupational mitigation.

Oxidative Stress & Haemolysis

As a disulfide, DADS redox-cycles: in the presence of glutathione and haemoglobin it generates hydrogen peroxide and damages erythrocytes in vitro, and di-, tri- and tetrasulfides all showed this, in the order tetra- > tri- > di- ^{3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →}. In rats, the tri- and tetrasulfides were the powerful haemolytic agents; DADS sits below them, but the mechanism is shared, and it is the same chemistry that explains Allium-induced haemolytic anaemia in dogs, cats and livestock ^{3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →}. Practically: this is a supra-dietary, isolate-level concern, and a reason not to treat concentrated garlic oil as a benign “more is better” supplement.

Enzyme & Drug Interactions

DADS is not pharmacologically inert toward drug metabolism. In rats it suppressed CYP2E1 and induced CYP2B1/2 with a phenobarbital-like profile, while raising glutathione transferases and UDP-glucuronosyltransferases ^{6Reference 6Siess MH et al. · 1997AnimalModification of hepatic drug-metabolizing enzymes in rats treated with alkyl sulfidesView study →}. CYP2E1 handles ethanol, paracetamol/acetaminophen, chlorzoxazone, halogenated anaesthetics and nitrosamines; sustained inhibition would shift their handling. Separately, DADS inhibits platelet aggregation in vitro ^{16Reference 16Chan KC et al. · 2002Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregationView study →}, and garlic’s antiplatelet reputation is already the basis for the standard advice to pause concentrated garlic products before surgery and to be cautious alongside anticoagulants. Neither interaction has been quantified in humans for the isolate.

What Is Not Characterised

There is no human toxicology package for isolated DADS — no established oral bioavailability, no repeat-dose human safety study, no defined intake limit. The rodent maximum tolerated dose used for chemoprevention work was 250 ppm in the diet ^{17Reference 17Reddy BS et al. · 1993Chemoprevention of colon carcinogenesis by organosulfur compoundsView study →}. Reproductive and developmental toxicity of the isolate has not been characterised; whether garlic products are appropriate in pregnancy or lactation is a decision that belongs to the herb or product page, where intake is actually chosen, not to a molecule page. Genotoxicity data are indirect and point the other way — DADS was antimutagenic in the Ames test against three ultimate carcinogens ^{4Reference 4Guyonnet D et al. · 2001Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme inductionView study →} — but that is not a completed safety assessment.

Safety at a Glance

⚠️ Moderate toxicity

• Ordinary culinary exposure is unremarkable. Garlic and garlic-flavoured food have a long history of safe use, and DADS is a permitted, widely used flavour compound.
• A well-documented contact allergen. Diallyl disulfide is a principal garlic sensitiser and a recognised cause of occupational hand dermatitis in cooks and food handlers, with photocontact allergy also reported ^{21,22,34Reference 21Papageorgiou C et al. · 1983Allergic contact dermatitis to garlic (Allium sativum L.)View study →Reference 22Bordel-Gómez MT · 2008Sensitivity to diallyl disulfide in a Spanish populationView study →Reference 34Fernández-Vozmediano JM et al. · 2000Allergic contact dermatitis from diallyl disulfideView study →}.
• Redox-active toward red cells at concentrated doses. The disulfide generates hydrogen peroxide with glutathione and haemoglobin; its tri- and tetrasulfide relatives are frank haemolytic agents in rats ^{3Reference 3Munday R et al. · 2003In vitroComparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivoView study →}.
• Plausible drug-metabolism interaction. DADS lowers CYP2E1 and raises CYP2B in rats — relevant in principle to alcohol, paracetamol and other CYP2E1 substrates; unquantified in humans ^{6Reference 6Siess MH et al. · 1997AnimalModification of hepatic drug-metabolizing enzymes in rats treated with alkyl sulfidesView study →}.
• Antiplatelet in vitro. Consistent with garlic’s bleeding-risk caution around anticoagulants and surgery ^{16Reference 16Chan KC et al. · 2002Protective effect of three diallyl sulphides against glucose-induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregationView study →}.
• No human dose, no isolate safety study. Oral bioavailability is unestablished and no human intake limit exists; concentrated garlic-oil supplements vary up to 33-fold in sulfide content ^{12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →}.

Dosage

There is no human dose for isolated diallyl disulfide, and none of the figures below is a recommendation. They are the research levels at which the effects here were produced.

Human exposure happens through food and through steam-distilled garlic-oil products, in which DADS is roughly 15–22% of the oil ^{24,25Reference 24Herrera-Calderon O et al. · 2021In vitroChemical constituents, in vitro antioxidant activity and in silico study on NADPH oxidase of Allium sativum L. (garlic) essential oilView study →Reference 25El-Sayed HS et al. · 2017Chemical composition and antimicrobial activity of garlic essential oils evaluated in organic solvent, emulsifying, and self-microemulsifying water based delivery systemsView study →}. Because commercial garlic oils have been found to vary 33-fold in total sulfide content between brands, “garlic oil” is not a dose ^{12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →}. Whole-garlic dosing guidance — fresh cloves, standardised powder, aged extract — belongs on the garlic monograph, and none of those preparations is a meaningful source of this molecule anyway ^{12Reference 12Lawson LD et al. · 1991Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic productsView study →}. These are doses studied in research and are not a personal recommendation.

References

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