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Category: flavoring agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | white to tan powder (est) |
| Assay: | 95.00 to 100.00 %
|
| Food Chemicals Codex Listed: | No |
| Specific Gravity: | 1.19100 @ 25.00 °C.
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| Refractive Index: | 1.54200 @ 20.00 °C.
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| Melting Point: | 214.00 to 216.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 300.00 to 301.00 °C. @ 760.00 mm Hg
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| Vapor Pressure: | 0.001000 mmHg @ 25.00 °C. |
| Flash Point: | 275.00 °F. TCC ( 135.00 °C. )
|
| logP (o/w): | 1.310 |
| Shelf Life: | 12.00 month(s) or longer if stored properly. |
| Storage: | refrigerate in tightly sealed containers. |
| Soluble in: |
| | water, slightly | | | water, 3.291e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
| |
| Odor Type: roasted |
| |
| | cooked roasted |
Odor Description: at 0.10 % in propylene glycol. | cooked roasted |
| |
| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | flavoring agents |
| IFRA Purity Specification: | < 0.1% free allyl alcohol |
| Recommendation for S-allyl-laevo-cysteine usage levels up to: | | | not for fragrance use.
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| |
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 30.00 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 2.00 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | ND (μg/person/day) |
| NOEL (No Observed Effect Level): | 250 (mg/kg bw per day) |
| Threshold of Concern: | 90 (μg/person/day) |
| Structure Class: | III |
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). |
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library |
| publication number: 23 |
| Click here to view publication 23 |
| | average usual ppm | average maximum ppm |
| baked goods: | 2.00000 | 25.00000 |
| beverages(nonalcoholic): | - | - |
| beverages(alcoholic): | - | - |
| breakfast cereal: | 2.00000 | 25.00000 |
| cheese: | 2.00000 | 25.00000 |
| chewing gum: | - | - |
| condiments / relishes: | 2.00000 | 25.00000 |
| confectionery froastings: | - | - |
| egg products: | - | - |
| fats / oils: | 2.00000 | 25.00000 |
| fish products: | 2.00000 | 25.00000 |
| frozen dairy: | - | - |
| fruit ices: | - | - |
| gelatins / puddings: | - | - |
| granulated sugar: | - | - |
| gravies: | 2.00000 | 25.00000 |
| hard candy: | - | - |
| imitation dairy: | 2.00000 | 25.00000 |
| instant coffee / tea: | 2.00000 | 25.00000 |
| jams / jellies: | - | - |
| meat products: | 2.00000 | 25.00000 |
| milk products: | - | - |
| nut products: | 2.00000 | 25.00000 |
| other grains: | - | - |
| poultry: | 2.00000 | 25.00000 |
| processed fruits: | - | - |
| processed vegetables: | 2.00000 | 25.00000 |
| reconstituted vegetables: | 2.00000 | 25.00000 |
| seasonings / flavors: | 2.00000 | 25.00000 |
| snack foods: | 2.00000 | 25.00000 |
| soft candy: | - | - |
| soups: | 2.00000 | 25.00000 |
| sugar substitutes: | - | - |
| sweet sauces: | - | - |
Safety References:
| European Food Safety Athority(EFSA): | Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
Flavouring Group Evaluation 91 (FGE.91): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev1 (2009) View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 91, Revision 1 (FGE.91Rev1): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev3 (2011) View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 91, Revision 2 (FGE.91Rev2): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by the JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev5 (2012) View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 91, Revision 3 (FGE.91Rev3): consideration of aliphatic, aromatic and a,ß-unsaturated sulfides and thiols evaluated by JECFA (53rd, 61st, 68th and 76th meetings), structurally related to substances in FGE.08Rev5 View page or View pdf |
| EPI System: | View |
| Chemical Carcinogenesis Research Information System: | Search |
| AIDS Citations: | Search |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 9793905 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WGK Germany: | 3 |
| | (2R)-2-amino-3-prop-2-enylsulfanylpropanoic acid |
| Chemidplus: | 0021593771 |
| RTECS: | HA2466200 for cas# 21593-77-1 |
References:
Other Information:
Potential Blenders and core components note
| |
| For Odor |
| alliaceous |
| | garlic oil china | FL/FR |
| cheesy |
| S-( | methyl thio) butyrate | FL/FR |
| citrus |
| | grapefruit mercaptan | FL/FR |
| coumarinic |
| | tonka bean oleoresin | FR |
| spicy |
| | ethyl vinyl ketone | FL/FR |
| | ferula assa-foetida absolute | FL/FR |
| | methyl 3-(methyl thio) propionate | FL/FR |
| 2- | methyl 5-(methyl thio) furan | FL/FR |
| | methyl mercaptan | FL/FR |
| 3-( | methyl thio) hexanol | FL/FR |
| |
| For Flavor |
| |
| No flavor group found for these |
| | allyl methyl disulfide | FL |
| | allyl methyl trisulfide | FL |
| | allyl propyl disulfide | FL |
| | allyl propyl sulfide | FL |
| | allyl propyl trisulfide | FL |
| | diethyl trisulfide | FL |
| 3,6- | diethyl-1,2,4,5-tetrathiane and 3,5-diethyl-1,2,4-trithiolane mixture 1% in vegetable oil triglyceri | FL |
| | diisopropyl sulfide | FL |
| | diisopropyl trisulfide | FL |
| | dimethyl tetrasulfide | FL |
| | dipropyl sulfide | FL |
| | ethyl isothiocyanate | FL |
| | ethyl methyl trisulfide | FL |
| | ethyl propyl disulfide | FL |
| | ethyl propyl trisulfide | FL |
| 3-( | ethyl thio) butanol | FL |
| (Z+E)-5- | ethyl-4-methyl-2-(2-butyl) thiazoline | FL |
| (Z+E)-5- | ethyl-4-methyl-2-(2-methyl propyl) thiazoline | FL |
| 4-( | methyl thio) butanol | FL |
| 1- | phenyl-3(5)-propyl pyrazole | FL |
| 3-iso | propenyl pentane dioic acid | FL |
| | thiophene | FL |
|
| 5- | acetyl-2,3-dihydro-1,4-thiazine | FL |
| (±)-3-( | methyl thio) heptanal | FL |
| 3-( | methyl thio) methyl thiophene | FL |
| 2- | methyl-1-methyl thio-2-butene | FL |
| | pyrrolidino-(1,2E)-4H-2,4-dimethyl-1,3,5-dithiazine | FL |
| alliaceous |
| | allyl disulfide | FL |
| | allyl mercaptan | FL |
| | allyl thiopropionate | FL |
| | benzyl mercaptan | FL |
| 1,3- | butane dithiol | FL |
| | cyclopentyl mercaptan | FL |
| | diethyl disulfide | FL |
| | dipropyl trisulfide | FL |
| | garlic oil china | FL/FR |
| 2- | methyl thioacetaldehyde | FL |
| 3- | tetrahydrothiophenone | FL |
| | truffle sulfide | FL |
| citrus |
| | grapefruit mercaptan | FL/FR |
| fatty |
| | dimethyl sulfoxide | FL |
| garlic |
| | allyl methyl sulfide | FL |
| | garlic oleoresin | FL |
| meaty |
| (R,S)-2- | mercapto-3-butanol | FL |
| | phenyl mercaptan | FL |
| | propyl 2-mercaptopropionate | FL |
| ortho- | thiocresol | FL |
| metallic |
| 3-( | methyl thio) hexanol | FL/FR |
| musty |
| 2- | methyl 5-(methyl thio) furan | FL/FR |
| S-( | methyl thio) butyrate | FL/FR |
| nutty |
| 2- | butyl-2-butenal | FL |
| onion |
| | methyl propyl disulfide | FL |
| | methyl propyl trisulfide | FL |
| | propyl thioacetate | FL |
| roasted |
| | ethyl 3-(furfuryl thio) propionate | FL |
| | hexyl mercaptan | FL |
| | lactoyl ethanolamine | FL |
| | lactoyl ethanolamine phosphate | FL |
| seafood |
| 1,4- | dithiane | FL |
| spicy |
| | ethyl vinyl ketone | FL/FR |
| sulfurous |
| | allyl sulfide | FL |
| | butyl mercaptan | FL |
| | diallyl polysulfides | FL |
| | diallyl tetrasulfide | FL |
| | diallyl trisulfide | FL |
| | ethyl methyl sulfide | FL |
| S- | ethyl thioacetate | FL |
| | ferula assa-foetida absolute | FL/FR |
| | furfuryl methyl sulfide | FL |
| | furfuryl thiopropionate | FL |
| | methyl mercaptan | FL/FR |
| 1-( | methyl thio)-2-butanone | FL |
| 2,4,6- | trithiaheptane 10% in triacetin | FL |
| vegetable |
| | methyl 3-(methyl thio) propionate | FL/FR |
| |
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| S- | allyl cysteine | | S- | allyl L-cysteine | | | allyl laevo-cysteine | | (2R)-3-( | allyl thio)-2-aminopropanoic acid | | S- | allyl-L-cysteine | | S- | allylcysteine | | (2R)-2- | amino-3-(prop-2-en-1-yl sulfanyl) propanoic acid | | (2R)-2- | amino-3-prop-2-enylsulfanylpropanoic acid | | | cysteine, S-2-propen-1-yl- | | L- | cysteine,S-2-propen-1-yl- | | L- | deoxyalliin | | S- | prop-2-en-1-ylcysteine | | S-2- | propenyl-L-cysteine | | S-2- | propenyl-laevo-cysteine |
Articles:
| PubMed: | Oral Administration of (S)-Allyl-l-Cysteine and Aged Garlic Extract to Rats: Determination of Metabolites and Their Pharmacokinetics. |
| PubMed: | EGFR gene regulation in colorectal cancer cells by garlic phytocompounds with special emphasis on S-Allyl-L-Cysteine Sulfoxide. |
| PubMed: | Thermolysis kinetics and thermal degradation compounds of alliin. |
| PubMed: | Evaluation of the Effects of S-Allyl-L-cysteine, S-Methyl-L-cysteine, trans-S-1-Propenyl-L-cysteine, and Their N-Acetylated and S-Oxidized Metabolites on Human CYP Activities. |
| PubMed: | Alliin Attenuated RANKL-Induced Osteoclastogenesis by Scavenging Reactive Oxygen Species through Inhibiting Nox1. |
| PubMed: | Molecular detection and in vitro antioxidant activity of S-allyl-L-cysteine (SAC) extracted from Allium sativum. |
| PubMed: | Taste-Active Maillard Reaction Products in Roasted Garlic (Allium sativum). |
| PubMed: | Protective Effects of AGE and Its Components on Neuroinflammation and Neurodegeneration. |
| PubMed: | PMK-S005 Alleviates Age-Related Gastric Acid Secretion, Inflammation, and Oxidative Status in the Rat Stomach. |
| PubMed: | Neuroprotective effect of S-allyl-l-cysteine derivatives against endoplasmic reticulum stress-induced cytotoxicity is independent of calpain inhibition. |
| PubMed: | Downregulation of importin-9 protects MCF-7 cells against apoptosis induced by the combination of garlic-derived alliin and paclitaxel. |
| PubMed: | Pharmacokinetics of S-Allyl-l-cysteine in Rats Is Characterized by High Oral Absorption and Extensive Renal Reabsorption. |
| PubMed: | S-allyl-L-cysteine and isoliquiritigenin improve mitochondrial function in cellular models of oxidative and nitrosative stress. |
| PubMed: | Gastroprotective Effects of PMK-S005 against Ethanol-Induced Acute Gastric Damage in Rats. |
| PubMed: | Identification of a flavin-containing S-oxygenating monooxygenase involved in alliin biosynthesis in garlic. |
| PubMed: | Enzymatic synthesis of γ-L-glutamyl-S-allyl-L-cysteine, a naturally occurring organosulfur compound from garlic, by Bacillus licheniformis γ-glutamyltranspeptidase. |
| PubMed: | Effective production of S-allyl-L-cysteine through a homogeneous reaction with activated endogenous γ-glutamyltranspeptidase in garlic (Allium Sativum). |
| PubMed: | Metabolism, excretion, and pharmacokinetics of S-allyl-L-cysteine in rats and dogs. |
| PubMed: | Garlic γ-glutamyl transpeptidases that catalyze deglutamylation of biosynthetic intermediate of alliin. |
| PubMed: | Protective effects of garlic extract, PMK-S005, against nonsteroidal anti-inflammatory drugs-induced acute gastric damage in rats. |
| PubMed: | S-allyl L-cysteine protects the retina against kainate excitotoxicity in the rat. |
| PubMed: | Development and validation of S-allyl-L-cysteine in rat plasma using a mixed-mode reversed-phase and cation-exchange LC-ESI-MS/MS method: application to pharmacokinetic studies. |
| PubMed: | Protective effect of S-allyl-L-cysteine against endoplasmic reticulum stress-induced neuronal death is mediated by inhibition of calpain. |
| PubMed: | Retraction. S-Allyl-L-cysteine sulfoxide inhibits tumor necrosis factor-alpha induced monocyte adhesion and intercellular cell adhesion molecule-1 expression in human umbilical vein endothelial cells. |
| PubMed: | Effect of processing and storage time on the contents of organosulfur compounds in pickled blanched garlic. |
| PubMed: | Effects of SAC on oxidative stress and NO availability in placenta: potential benefits to preeclampsia. |
| PubMed: | The effects and underlying mechanisms of S-allyl l-cysteine treatment of the retina after ischemia/reperfusion. |
| PubMed: | Alliinase from Ensifer adhaerens and Its Use for Generation of Fungicidal Activity. |
| PubMed: | The "aged garlic extract:" (AGE) and one of its active ingredients S-allyl-L-cysteine (SAC) as potential preventive and therapeutic agents for Alzheimer's disease (AD). |
| PubMed: | [Effect of S-allyl-L-cysteine on isolate heart subject to ischemia/reperfusion]. |
| PubMed: | Effects of s-allyl-L-cysteine on cell proliferation and neuroblast differentiation in the mouse dentate gyrus. |
| PubMed: | Oxidative insults to neurons and synapse are prevented by aged garlic extract and S-allyl-L-cysteine treatment in the neuronal culture and APP-Tg mouse model. |
| PubMed: | Palladium(II) complex with S-allyl-L-cysteine: new solid-state NMR spectroscopic measurements, molecular modeling and antibacterial assays. |
| PubMed: | Garlic flavonoids and organosulfur compounds: impact on the hepatic pharmacokinetics of saquinavir and darunavir. |
| PubMed: | 3-(allyltrisulfanyl)-2-aminopropanoic acid, a novel nonvolatile water-soluble antimicrobial sulfur compound in heated garlic. |
| PubMed: | S-allyl-L-cysteine sulfoxide inhibits tumor necrosis factor-alpha induced monocyte adhesion and intercellular cell adhesion molecule-1 expression in human umbilical vein endothelial cells. |
| PubMed: | Protective effects of cysteine analogues on acute myocardial ischemia: novel modulators of endogenous H(2)S production. |
| PubMed: | S-allyl L-cysteine diminishes cerebral ischemia-induced mitochondrial dysfunctions in hippocampus. |
| PubMed: | Purification and characterization of flavin-containing monooxygenase isoform 3 from rat kidney microsomes. |
| PubMed: | Unusual cystine lyase activity of the enzyme alliinase: direct formation of polysulphides. |
| PubMed: | Anti-amyloidogenic activity of S-allyl-L-cysteine and its activity to destabilize Alzheimer's beta-amyloid fibrils in vitro. |
| PubMed: | Amyloid beta-protein potentiates tunicamycin-induced neuronal death in organotypic hippocampal slice cultures. |
| PubMed: | Role of caspase-12 in amyloid beta-peptide-induced toxicity in organotypic hippocampal slices cultured for long periods. |
| PubMed: | Two structures of alliinase from Alliium sativum L.: apo form and ternary complex with aminoacrylate reaction intermediate covalently bound to the PLP cofactor. |
| PubMed: | S-Allyl-L-cysteine attenuates cerebral ischemic injury by scavenging peroxynitrite and inhibiting the activity of extracellular signal-regulated kinase. |
| PubMed: | Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds. |
| PubMed: | Dietary S-allyl-L-cysteine reduces mortality with decreased incidence of stroke and behavioral changes in stroke-prone spontaneously hypertensive rats. |
| PubMed: | Changes in organosulfur compounds in garlic cloves during storage. |
| PubMed: | N-acetylcysteine selectively protects cerebellar granule cells from 4-hydroxynonenal-induced cell death. |
| PubMed: | Comparative study of endoplasmic reticulum stress-induced neuronal death in rat cultured hippocampal and cerebellar granule neurons. |
| PubMed: | Redox-sensitive proteins are potential targets of garlic-derived mercaptocysteine derivatives. |
| PubMed: | In vitro interactions of water-soluble garlic components with human cytochromes p450. |
| PubMed: | Aged garlic extract and its constituents inhibit platelet aggregation through multiple mechanisms. |
| PubMed: | 1H-15N NMR studies of the complex bis(S-allyl-L-cysteinate)palladium(II). |
| PubMed: | Model studies on precursor system generating blue pigment in onion and garlic. |
| PubMed: | Aminotransferase, L-amino acid oxidase and beta-lyase reactions involving L-cysteine S-conjugates found in allium extracts. Relevance to biological activity? |
| PubMed: | Inhibition of tumor growth by a novel approach: in situ allicin generation using targeted alliinase delivery. |
| PubMed: | S-allyl-L-cysteine selectively protects cultured rat hippocampal neurons from amyloid beta-protein- and tunicamycin-induced neuronal death. |
| PubMed: | Neurotoxicity induced by amyloid beta-peptide and ibotenic acid in organotypic hippocampal cultures: protection by S-allyl-L-cysteine, a garlic compound. |
| PubMed: | Protective effect of S-allyl-L-cysteine, a garlic compound, on amyloid beta-protein-induced cell death in nerve growth factor-differentiated PC12 cells. |
| PubMed: | High-performance ion-pair chromatography method for simultaneous analysis of alliin, deoxyalliin, allicin and dipeptide precursors in garlic products using multiple mass spectrometry and UV detection. |
| PubMed: | Sulfoxides as urinary metabolites of S-allyl-L-cysteine in rats: evidence for the involvement of flavin-containing monooxygenases. |
| PubMed: | Biomonitoring the intake of garlic via urinary excretion of allyl mercapturic acid. |
| PubMed: | N alpha-(1-deoxy-D-fructos-1-yl)-L-arginine, an antioxidant compound identified in aged garlic extract. |
| PubMed: | Methionine S-oxidation in human and rabbit liver microsomes: evidence for a high-affinity methionine S-oxidase activity that is distinct from flavin-containing monooxygenase 3. |
| PubMed: | Allyl-containing sulfides in garlic increase uncoupling protein content in brown adipose tissue, and noradrenaline and adrenaline secretion in rats. |
| PubMed: | Species and sex differences in expression of flavin-containing monooxygenase form 3 in liver and kidney microsomes. |
| PubMed: | The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins. |
| PubMed: | Neurotrophic activity of organosulfur compounds having a thioallyl group on cultured rat hippocampal neurons. |
| PubMed: | Cysteine-S-conjugate beta-lyase activity and pyridoxal phosphate binding site of onion alliin lyase. |
| PubMed: | Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA-expressed flavin-containing mono-oxygenases: studies with S-(1,2-dichlorovinyl)-L-cysteine, S-(1,2,2-trichlorovinyl)-L-cysteine, S-allyl-L-cysteine, and S-benzyl-L-cysteine. |
| PubMed: | New agents for cancer chemoprevention. |
| PubMed: | Urinary excretion of N-acetyl-S-allyl-L-cysteine upon garlic consumption by human volunteers. |
| PubMed: | On the Isolation and Characterization of a C-S-Lyase Preparation from Leek,Allium porrum. |
| PubMed: | A novel amino acid glycoside and three amino acids from Allium sativum. |
| PubMed: | Interspecific hybrid between Allium cepa and Allium sativum. |
| PubMed: | The acute effects of S-(1,2-dichlorovinyl)-L-cysteine and related chemicals on renal function and ultrastructure in the pentobarbital-anesthetized dog: structure-activity relationships, biotransformation, and unique site-specific nephrotoxicity. |
| PubMed: | HPLC of S-Alk(en)yl-L-cysteine Derivatives in Garlic including Quantitative Determination of (+)-S-Allyl-L-cysteine Sulfoxide (Alliin). |
| PubMed: | Studies on the antimutagenic activities of garlic extract. |
| PubMed: | The C-S lyases of higher plants: preparation and properties of homogeneous alliin lyase from garlic (Allium sativum). |
| PubMed: | Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein. |
| PubMed: | Purification of the alliin lyase of garlic, Allium sativum L. |
| PubMed: | gama-L-Glutamyl-S-allyl-L-cysteine, a new gama-glutamyl peptide in garlic. |
|