Identification

Nameallicin
IUPAC3-prop-2-enylsulfinylsulfanylprop-1-ene
CAS Number539-86-6
EINECS208-727-7
FDA UNII3C39BY17Y6
Molecular FormulaC6 H10 O S2
Molecular Weight162.27490000
Nikkaji NumberJ71.032F
Beilstein1752823

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 1.11200 @ 20.00 °C.
Refractive Index 1.56100 @ 20.00 °C.
Boiling Point 248.60 °C. @ 760.00 mm Hg (est)
Vapor Pressure 0.038000 mmHg @ 25.00 °C. (est)
Flash Point 219.00 °F. TCC ( 104.20 °C. ) (est)
logP (o/w) 1.133 (est)
Soluble in water, 2.40E+04 mg/L @ 10 °C (exp)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintravenous-mouse LD50 60 mg/kg
Dermal Toxicitysubcutaneous-mouse LD50 120 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
IFRA Purity Specification< 0.1% free allyl alcohol
Recommendation for allicin usage levels up tonot for fragrance use.
Recommendation for allicin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

garlic garlic bulb garlic oil onion onion bulb

Synonyms

S- allyl 2-propene-1-sulfinothioate S- allyl acrylo-1-sulfinothioate S- allyl acrylo-1-sulphinothioate S- allyl prop-2-ene-1-sulfinothioate allyl sulfinyl-allyl sulfide allyl thiosulfinic acid allyl ester allylthiosulphinic acid allyl ester diallyl thiosulfinate S- prop-2-en-1-yl prop-2-ene-1-sulfinothioate 3- prop-2-enylsulfinylsulfanylprop-1-ene 2- propene-1-sulfinic acid, thio-, S-allyl ester 2- propene-1-sulfinothioic acid S-2-propenyl ester 2- propene-1-sulfinothioic acid, S-2-propen-1-yl ester 2- propene-1-sulfinothioic acid, S-2-propenyl ester (9CI) thio-2-propene-1-sulfinic acid S-allyl ester PubMed: Allium sativum: facts and myths regarding human health PubMed: Bioactive Compounds and Biological Functions of Garlic (Allium sativum L.) PubMed: Chemical Constituents and Pharmacological Activities of Garlic (Allium sativum L.): A Review PubMed: Garlic PubMed: Allicin Regulates Energy Homeostasis through Brown Adipose Tissue PubMed: Black garlic: A critical review of its production, bioactivity, and application PubMed: Allicin-induced host-gut microbe interactions improves energy homeostasis PubMed: Allicin alleviates acrylamide-induced oxidative stress in BRL-3A cells PubMed: Plant Phytochemicals in Food Preservation: Antifungal Bioactivity: A Review PubMed: Physicochemical Properties, Biological Activity, Health Benefits, and General Limitations of Aged Black Garlic: A Review PubMed: Garlic (Allium sativum L.): a potential unique therapeutic food rich in organosulfur and flavonoid compounds to fight with COVID-19 PubMed: Effect of allicin and its mechanism of action in purine removal in turbot PubMed: ?-Lactoglobulin as nanotransporter for allicin: Sensory properties and applicability in food PubMed: Allicin alleviated acrylamide-induced NLRP3 inflammasome activation via oxidative stress and endoplasmic reticulum stress in Kupffer cells and SD rats liver PubMed: Chemical composition and bioactive compounds of garlic (Allium sativum L.) as affected by pre- and post-harvest conditions: A review PubMed: Dietary Allicin Improved the Survival and Growth of Large Yellow Croaker (Larimichthys crocea) Larvae via Promoting Intestinal Development, Alleviating Inflammation and Enhancing Appetite PubMed: Allicin induces beige-like adipocytes via KLF15 signal cascade PubMed: The Mechanism in Gastric Cancer Chemoprevention by Allicin PubMed: Contribution of 2-Propenesulfenic Acid to the Antioxidant Activity of Allicin PubMed: Allicin Inhibited Staphylococcus aureus -Induced Mastitis by Reducing Lipid Raft Stability via LxRà in Mice PubMed: Allicin Modifies the Composition and Function of the Gut Microbiota in Alcoholic Hepatic Steatosis Mice PubMed: Downregulating PI3K/Akt/NF-?B signaling with allicin for ameliorating the progression of osteoarthritis: in vitro and vivo studies PubMed: Allicin enhances the radiosensitivity of colorectal cancer cells via inhibition of NF-?B signaling pathway PubMed: Allicin inhibits transient outward potassium currents in mouse ventricular myocytes PubMed: Preparation of allicin-whey protein isolate conjugates: Allicin extraction by water, conjugates' ultrasound-assisted binding and its stability, solubility and emulsibility analysis PubMed: Allicin Inhibits Glutamate Release from Rat Cerebral Cortex Nerve Terminals Through Suppressing Ca(2+) Influx and Protein Kinase C Activity PubMed: S-ethyl ethanethiosulfinate, a derivative of allicin, induces metacaspase-dependent apoptosis through ROS generation in Penicillium chrysogenum PubMed: Allicin inhibits osteoblast apoptosis and steroid-induced necrosis of femoral head progression by activating the PI3K/AKT pathway PubMed: Plant nutraceuticals as antimicrobial agents in food preservation: terpenoids, polyphenols and thiols PubMed: Allicin relaxes isolated mesenteric arteries through activation of PKA-K(ATP) channel in rat PubMed: Protective effects of allicin on streptozotocin-induced diabetic nephropathy in rats PubMed: Protective effects of allicin on 1,3-DCP-induced lipid metabolism disorder in HepG2 cells PubMed: Analyzing the antibacterial effects of food ingredients: model experiments with allicin and garlic extracts on biofilm formation and viability of Staphylococcus epidermidis PubMed: A review of the cardiovascular benefits and antioxidant properties of allicin PubMed: Cholesterol-lowering effect of allicin on hypercholesterolemic ICR mice PubMed: Garlic allicin as a potential agent for controlling oral pathogens PubMed: Allicin modulates the antioxidation and detoxification capabilities of primary rat hepatocytes PubMed: Allicin inhibits lymphangiogenesis through suppressing activation of vascular endothelial growth factor (VEGF) receptor PubMed: Intake of garlic and its bioactive components PubMed: Endoplasmic Reticulum Stress and Unfolded Protein Response Pathways Involved in the Health-Promoting Effects of Allicin on the Jejunum PubMed: The Disulfide Stress Response and Protein S-thioallylation Caused by Allicin and Diallyl Polysulfanes in Bacillus subtilis as Revealed by Transcriptomics and Proteomics PubMed: Self-Assembling Cyclodextrin-Based Nanoparticles Enhance the Cellular Delivery of Hydrophobic Allicin PubMed: Allicin induces p53-mediated autophagy in Hep G2 human liver cancer cells PubMed: Effect of dietary à-ketoglutarate and allicin supplementation on the composition and diversity of the cecal microbial community in growing pigs PubMed: Allicin purified from fresh garlic cloves induces apoptosis in colon cancer cells via Nrf2 PubMed: Is allicin able to reduce Campylobacter jejuni colonization in broilers when added to drinking water? PubMed: Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability PubMed: Studies on purification of allicin by molecular distillation PubMed: Protective effect of allicin against acrylamide-induced hepatocyte damage in vitro and in vivo PubMed: Allicin protects rat cardiomyoblasts (H9c2 cells) from hydrogen peroxide-induced oxidative injury through inhibiting the generation of intracellular reactive oxygen species PubMed: Diet Supplementation with Allicin Protects against Alcoholic Fatty Liver Disease in Mice by Improving Anti-inflammation and Antioxidative Functions PubMed: Allicin protects spinal cord neurons from glutamate-induced oxidative stress through regulating the heat shock protein 70/inducible nitric oxide synthase pathway PubMed: Allicin induces anti-human liver cancer cells through the p53 gene modulating apoptosis and autophagy PubMed: Low allicin release from garlic supplements: a major problem due to the sensitivities of alliinase activity PubMed: The effects of thiosulfinates on methane production from anaerobic co-digestion of waste activated sludge and food waste and mitigate method PubMed: Dietary phytochemicals and human health PubMed: Use of allicin as feed additive to enhance vaccination capacity of Clostridium perfringens toxoid in rabbits PubMed: Hyperspectral imaging for predicting the allicin and soluble solid content of garlic with variable selection algorithms and chemometric models PubMed: Allicin and derivates are cysteine protease inhibitors with antiparasitic activity PubMed: The effects of allicin on weight in fructose-induced hyperinsulinemic, hyperlipidemic, hypertensive rats PubMed: Efficacy of allicin in decreasing lead (Pb) accumulation in selected tissues of lead-exposed common carp (Cyprinus carpio) PubMed: Garlic: empiricism or science? PubMed: Molecular approaches toward targeted cancer prevention with some food plants and their products: inflammatory and other signal pathways PubMed: Quantitative determination of allicin in garlic: supercritical fluid extraction and standard addition of alliin PubMed: Biological and chemical stability of garlic-derived allicin PubMed: Characteristics, biosynthesis, decomposition, metabolism and functions of the garlic odour precursor, S-allyl-L-cysteine sulfoxide PubMed: Influence of pH, concentration and light on stability of allicin in garlic (Allium sativum L.) aqueous extract as measured by UPLC PubMed: Antimicrobial properties of allium species PubMed: Quantification of allicin by high performance liquid chromatography-ultraviolet analysis with effect of post-ultrasonic sound and microwave radiation on fresh garlic cloves PubMed: The Potential for Plant Derivatives against Acrylamide Neurotoxicity PubMed: Effects of dietary patterns combined with dietary phytochemicals on breast cancer metastasis PubMed: Healthy and adverse effects of plant-derived functional metabolites: the need of revealing their content and bioactivity in a complex food matrix PubMed: Salting-out extraction of allicin from garlic (Allium sativum L.) based on ethanol/ammonium sulfate in laboratory and pilot scale PubMed: Raw garlic consumption is inversely associated with prehypertension in a large-scale adult population PubMed: The Garlic Compound Z-Ajoene, S-Thiolates COX2 and STAT3 and Dampens the Inflammatory Response in RAW264.7 Macrophages PubMed: Potential protective effects of oral administration of allicin on acrylamide-induced toxicity in male mice PubMed: ?-Lactoglobulin as nanotransporter--Part II: Characterization of the covalent protein modification by allicin and diallyl disulfide PubMed: A Mini HIP HOP Assay Uncovers a Central Role for Copper and Zinc in the Antifungal Mode of Action of Allicin PubMed: Comparative UHPLC-Q-Orbitrap HRMS-Based Metabolomics Unveils Biochemical Changes of Black Garlic during Aging Process PubMed: Prophylactic Potential of Conventional and Supercritical Garlic Extracts to Alleviate Diet Related Malfunctions PubMed: Anticancer potential of garlic and its bioactive constituents: A systematic and comprehensive review PubMed: Diallyl Trisulfide Inhibits Platelet Aggregation through the Modification of Sulfhydryl Groups PubMed: Anti-oncogenic perspectives of spices/herbs: A comprehensive review PubMed: Profiling of organosulfur compounds and amino acids in garlic from different regions of China PubMed: Comparison of Physicochemical Characteristics of Garlic Produced from South Korea and China PubMed: Garlic: nature's protection against physiological threats PubMed: Some Physiological and Biochemical Mechanisms during Seed-to-Seedling Transition in Tomato as Influenced by Garlic Allelochemicals PubMed: Development and Metabolite Profiling of Elephant Garlic Vinegar PubMed: The antioxidant properties of garlic compounds: allyl cysteine, alliin, allicin, and allyl disulfide PubMed: Freeze-dried, oven-dried, and microencapsulation of essential oil from Allium sativum as potential preservative agents of minced meat PubMed: In Vitro and Cryopreservation Techniques for Conservation of Snow Mountain Garlic PubMed: Reactivity of allyl methyl sulphide, the in-vitro metabolite of garlic, with some amino acids and with phospholipid involved in viral infections PubMed: Allium sativum L. (Garlic) bulb enlargement as influenced by differential combinations of photoperiod and temperature PubMed: pH Reversibly Switchable Nanocapsule for Bacteria-Targeting Near-Infrared Fluorescence Imaging-Guided Precision Photodynamic Sterilization PubMed: Sonication, osmosonication and vacuum-assisted osmosonication pretreatment of Ghanaian garlic slices: Effect on physicochemical properties and quality characteristics PubMed: Influence of garlic and pepper powder on physicochemical and sensory qualities of flavoured rice noodle PubMed: Controlled Fermentation Using Autochthonous Lactobacillus plantarum Improves Antimicrobial Potential of Chinese Chives against Poultry Pathogens PubMed: The investigation of detection and sensing mechanism of spicy substance based on human TRPV1 channel protein-cell membrane biosensor PubMed: Comparison of two extraction methods (high pressure extraction vs. maceration) for the total and relative amount of hydrophilic and lipophilic organosulfur compounds in garlic cloves and stems. An applicati PubMed: Garlic as an anti-diabetic agent: recent progress and patent reviews PubMed: ?-Lactoglobulin as nanotransporter--Part I: Binding of organosulfur compounds PubMed: Short-term heating reduces the anti-inflammatory effects of fresh raw garlic extracts on the LPS-induced production of NO and pro-inflammatory cytokines by downregulating allicin activity in RAW 264.7 macro PubMed: Influence of Two Garlic-Derived Compounds, Propyl Propane Thiosulfonate (PTS) and Propyl Propane Thiosulfinate (PTSO), on Growth and Mycotoxin Production by Fusarium Species In Vitro and in Stored Cereals PubMed: Novel ultrasonic-assisted vacuum drying technique for dehydrating garlic slices and predicting the quality properties by low field nuclear magnetic resonance PubMed: Determination of allicin, S-allylcysteine and volatile metabolites of garlic in breath, plasma or simulated gastric fluids PubMed: Polysulfides as biologically active ingredients of garlic PubMed: Effect of blanching and freezing on the physical properties, bioactive compounds, and microstructure of garlic (Allium sativum L.) PubMed: Effects of temperature on the quality of black garlic PubMed: Antithrombotic and anticancer effects of garlic-derived sulfur compounds: a review PubMed: Screening of cytoprotectors against methotrexate-induced cytogenotoxicity from bioactive phytochemicals PubMed: Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals PubMed: Retention of Bioactive Compounds During Domestic Processing of Croatian Domestic Garlic (Allium sativum L.) PubMed: Effect of catalytic infrared dry-blanching on the processing and quality characteristics of garlic slices PubMed: In Vitro and In Vivo Control of Secondary Bacterial Infection Caused by Leishmania major PubMed: Encapsulations of wild garlic (Allium ursinum L.) extract using spray congealing technology PubMed: Hypocholesterolemic effect of an enteric-coated garlic supplement PubMed: Vacuum pretreatment coupled to ultrasound assisted osmotic dehydration as a novel method for garlic slices dehydration PubMed: Antioxidant effects of supercritical fluid garlic extracts in canned artichokes PubMed: Antioxidant effects of supercritical fluid garlic extracts in sunflower oil PubMed: Anti-Cancer Potential of Homemade Fresh Garlic Extract Is Related to Increased Endoplasmic Reticulum Stress PubMed: Molecular targets of dietary agents for prevention and therapy of cancer PubMed: Cooked garlic and antioxidant activity: Correlation with organosulfur compound composition PubMed: Changes in nutritional and bio-functional compounds and antioxidant capacity during black garlic processing PubMed: Methyl jasmonate and low temperature can help for keeping some physicochemical quality parameters in garlic (Allium sativum L.) cloves PubMed: Effect of pre-storage removal of different parts of the scape top on the biochemical changes of two garlic cultivars during controlled atmosphere storage PubMed: Data on the effect of boiling on the organosulfides and the hydrogen sulfide-releasing activity of garlic PubMed: Changes of S-Allylmercaptocysteine and ?-Glutamyl- S-allylmercaptocysteine Contents and Their Putative Production Mechanisms in Garlic Extract during the Aging Process PubMed: Boiling enriches the linear polysulfides and the hydrogen sulfide-releasing activity of garlic PubMed: Low-frequency and low-intensity ultrasound accelerates alliinase-catalysed synthesis of allicin in freshly crushed garlic PubMed: A Comparative Study of Allium Hirtifolium in Traditional and Modern Medicine PubMed: Physicochemical characteristics of complexes between amylose and garlic bioactive components generated by milling activating method PubMed: Antioxidant and antimicrobial activities of commercial rice wine extracts of Taiwanese Allium fistulosum PubMed: Effect of porphobilinogen on the formation of garlic green pigments PubMed: Sulfur compounds identification and quantification from Allium spp. fresh leaves PubMed: Development and characterization of phosphatidylcholine nanovesicles, containing garlic extract, with antilisterial activity in milk PubMed: Protective effects of diallyl disulfide against acetaminophen-induced nephrotoxicity: A possible role of CYP2E1 and NF-?B PubMed: Enterobacter aerogenes ZDY01 Attenuates Choline-Induced Trimethylamine N-Oxide Levels by Remodeling Gut Microbiota in Mice PubMed: Effect of different combined mechanical and thermal treatments on the quality characteristics of garlic paste PubMed: Evaluation of Protective Effects of Bioactive Phytochemicals Against Methotrexate in Salmonella typhimurium TA1535/pSK1002 Coupled with Micronucleus Assay PubMed: Post-harvest control of gray mold in table grapes using volatile sulfur compounds from Allium sativum PubMed: Inhibition of platelet activation by lachrymatory factor synthase (LFS)-silenced (tearless) onion juice PubMed: Effect of garlic and allium-derived products on the growth and metabolism of Spironucleus vortens PubMed: Modulation of programmed cell death by medicinal plants PubMed: Effect of garlic supplement in the management of type 2 diabetes mellitus (T2DM): a meta-analysis of randomized controlled trials PubMed: Evaluating the anti-neuroinflammatory capacity of raw and steamed garlic as well as five organosulfur compounds PubMed: S-allyl-mercapto-captopril: a novel compound in the treatment of Cohen-Rosenthal diabetic hypertensive rats PubMed: In vitro phytotherapy of vector snails by binary combinations of larvicidal active components in effective control of fascioliasis PubMed: Biochemical Characterization and Antimicrobial and Antifungal Activity of Two Endemic Varieties of Garlic (Allium sativum L.) of the Campania Region, Southern Italy PubMed: Aged garlic extract ameliorates immunotoxicity, hematotoxicity and impaired burn-healing in malathion- and carbaryl-treated male albino rats PubMed: Development of garlic bioactive compounds analytical methodology based on liquid phase microextraction using response surface design. Implications for dual analysis: Cooked and biological fluids samples PubMed: Garlic extracts prevent oxidative stress, hypertrophy and apoptosis in cardiomyocytes: a role for nitric oxide and hydrogen sulfide PubMed: Correlation between antioxidant activity of garlic extracts and WEHI-164 fibrosarcoma tumor growth in BALB/c mice PubMed: Traceability of Italian garlic (Allium sativum L.) by means of HRMAS-NMR spectroscopy and multivariate data analysis PubMed: Selection of functional lactic acid bacteria as starter cultures for the fermentation of Korean leek (Allium tuberosum Rottler ex Sprengel.) PubMed: Antioxidant and Anticoagulant Status Were Improved by Personalized Dietary Intervention Based on Biochemical and Clinical Parameters in Cancer Patients PubMed: Therapeutic actions of allylmercaptocaptopril and captopril in a rat model of metabolic syndrome PubMed: Use of a substrate/alliinase combination to generate antifungal activity in situ PubMed: Composition, stability, and bioavailability of garlic products used in a clinical trial PubMed: Aqueous garlic extracts prevent oxidative stress and vascular remodeling in an experimental model of metabolic syndrome PubMed: Effects of garlic oil on platelet aggregation: a double-blind placebo-controlled crossover study PubMed: Effect of garlic powder tablet on carotid intima-media thickness in patients with coronary artery disease: a preliminary randomized controlled trial PubMed: Effect of cooking on garlic (Allium sativum L.) antiplatelet activity and thiosulfinates content PubMed: Improving knowledge of garlic paste greening through the design of an experimental strategy PubMed: Applications of direct analysis in real time mass spectrometry (DART-MS) in Allium chemistry. 2-propenesulfenic and 2-propenesulfinic acids, diallyl trisulfane S-oxide, and other reactive sulfur compounds f PubMed: Protective effects of garlic sulfur compounds against DNA damage induced by direct- and indirect-acting genotoxic agents in HepG2 cells PubMed: Differential inhibition of human platelet aggregation by selected Allium thiosulfinates PubMed: Identification of two novel pigment precursors and a reddish-purple pigment involved in the blue-green discoloration of onion and garlic PubMed: Growth and health of Holstein calves fed milk replacers supplemented with antibiotics or Enteroguard PubMed: Allium chemistry: identification of organosulfur compounds in ramp (Allium tricoccum) homogenates PubMed: The determination of metabolites of garlic preparations in breath and human plasma PubMed: Effects of garlic (Allium sativum L.) supplementation on cytochrome P450 2D6 and 3A4 activity in healthy volunteers PubMed: Properties and storage stability of whey protein edible film with spice powders PubMed: Determination of added sulfites in dried garlic with a modified version of the optimized Monier-Williams method PubMed: Supercritical fluid chromatography of garlic (Allium sativum) extracts with mass spectrometric identification of allicin PubMed: Parallel analysis of global garlic gene expression and alliin content following leaf wounding PubMed: Solid phase microextraction coupled to liquid chromatography. Analysis of organosulphur compounds avoiding artifacts formation PubMed: Determination of sulfite in dried garlic by reversed-phase ion-pairing liquid chromatography with post-column detection PubMed: [Pharmaceutical significance of Allium sativum L. 4. Antifungal effects] PubMed: Variability of solids, organosulfur compounds, pungency and health-enhancing traits in garlic (Allium sativum L.) cultivars belonging to different ecophysiological groups PubMed: Cinnamaldehyde Could Reduce the Accumulation of Diarrhetic Shellfish Toxins in the Digestive Gland of the Mussel Perna viridis under Laboratory Conditions PubMed: Chemical and Genetic Evaluation of Somaclonal Variants of Egyptian Garlic (Allium sativum L.) PubMed: Garlic may soon rival commercial antibiotics