Record Information
Version1.0
Creation date2010-04-08 22:10:02 UTC
Update date2019-11-26 03:06:22 UTC
Primary IDFDB012196
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDi-2-propenyl disulfide, 9CI
DescriptionDi-2-propenyl disulfide, 9CI or simply allyl disulfide is a principal constituent of garlic (Allium sativum). It is found in in onion (Allium cepa), ramsons (Allium ursinum), chive (Allium schoenoprasum) and Chinese chives (Allium tuberosum). It is also found in raw cabbage and seeds of herb-Sophia (Descurainia sophia). It can be used as a flavouring ingredient. Allyl disulfide is a potential nutriceutical.
CAS Number2179-57-9
Structure
Thumb
Synonyms
SynonymSource
2-Propenyl disulphideChEBI
3,3'-Disulfanediylbis(prop-1-ene)ChEBI
3,3'-Dithiobis(prop-1-ene)ChEBI
3-(Allyldisulfanyl)-1-propeneChEBI
4,5-Dithia-1,7-octadieneChEBI
Allyl disulfideChEBI
Diallyl disulphideChEBI
2-Propenyl disulfideGenerator
3,3'-Disulphanediylbis(prop-1-ene)Generator
3-(Allyldisulphanyl)-1-propeneGenerator
Allyl disulphideGenerator
Diallyl disulfideGenerator
Di-2-propenyl disulphide, 9ciGenerator
FEMA 2028HMDB
Garlicin?HMDB
AllitinHMDB
GarlicinHMDB
Allyll disulfideHMDB
1,2-(2-Propenyl)-disulphaneHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.74ALOGPS
logP2.76ChemAxon
logS-3.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity45.42 m³·mol⁻¹ChemAxon
Polarizability16.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H10S2
IUPAC name3-(prop-2-en-1-yldisulfanyl)prop-1-ene
InChI IdentifierInChI=1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2
InChI KeyPFRGXCVKLLPLIP-UHFFFAOYSA-N
Isomeric SMILESC=CCSSCC=C
Average Molecular Weight146.274
Monoisotopic Molecular Weight146.0223917
Classification
Description Belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassAllyl sulfur compounds
Sub ClassNot Available
Direct ParentAllyl sulfur compounds
Alternative Parents
Substituents
  • Allyl sulfur compound
  • Dialkyldisulfide
  • Organic disulfide
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 49.27%; H 6.89%; S 43.84%DFC
Melting PointNot Available
Boiling PointBp16 78-80°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd154 1.01DFC
Refractive Indexn20D 1.5410DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-42fd8ee78e535ee254d12015-03-01View Spectrum
GC-MS1,2-(2-Propenyl)-disulfane, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4339fab2bebf0f0edeadSpectrum
GC-MS1,2-(2-Propenyl)-disulfane, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4339fab2bebf0f0edeadSpectrum
Predicted GC-MS1,2-(2-Propenyl)-disulfane, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-3c9e908cce8cd1e879b1Spectrum
Predicted GC-MS1,2-(2-Propenyl)-disulfane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3900000000-9c371e3186390c01f0012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9400000000-b59d5745fd0de15330c42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0096-9000000000-19b665839042f6ee1fe92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-8ce4d0f7b3fe00f0be042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9100000000-b1cb4486db4015ba60512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdx-9200000000-c21f3e04b48075ba35b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9200000000-405bb2d5265314dcf9402021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-f1b1fa16e4f4df7e897a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02mi-9000000000-3ad51ebb7ed9cc9fe39b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-5900000000-ad48a60217abba68e11d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9100000000-cae86b0a41c4ddeda9f32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9000000000-8f43dc3308ac3b6182452021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08369
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID4488
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHFB14-R:HFB14-R
EAFUS ID105
Dr. Duke IDDIALLYL-DISULFIDE|ALLYL-DISULFIDE
BIGG IDNot Available
KNApSAcK IDC00001243
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1002791
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti lipemicAn agent that prevents or counteracts the accumulation of fatty substances in the blood, playing a biological role in lipid metabolism regulation. Therapeutically, it is used to manage hyperlipidemia, reducing the risk of cardiovascular disease, and is commonly applied in treating conditions such as high cholesterol and atherosclerosis.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-proliferativeAn agent that inhibits cell growth and division, particularly in cancer cells, preventing tumor expansion. It plays a biological role in regulating cell cycles and has therapeutic applications in cancer treatment, such as chemotherapy and targeted therapy, with key medical uses in managing various types of cancer and other proliferative diseases.DUKE
Anti-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Arylamine-N-acetyltransferase inhibitor23924 An agent that blocks the activity of arylamine-N-acetyltransferase, an enzyme involved in xenobiotic metabolism. It has therapeutic applications in reducing toxicity and carcinogenicity of certain chemicals, with key medical uses in cancer prevention and treatment of chemical-induced diseases.DUKE
Avifuge25944 An anthelmintic agent that expels parasitic worms, particularly tapeworms, from the body. Its therapeutic applications include treating intestinal worm infestations, with key medical uses in managing parasitic infections and promoting gastrointestinal health.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Name48318 flavorDUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Glucuronosyltransferase inducerAn agent that stimulates glucuronosyltransferase, enhancing glucuronidation reactions. It increases metabolism and clearance of toxins and drugs, with therapeutic applications in managing drug toxicity and certain cancers, and key medical uses in chemotherapy and detoxification.DUKE
HemolyticAn agent that ruptures red blood cells, playing a biological role in breaking down outdated or damaged cells. Therapeutically, it is used to treat conditions like malaria and certain blood disorders. Key medical uses include managing paroxysmal nocturnal hemoglobinuria and other hemolytic diseases, often requiring careful administration to avoid adverse effects.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
Hypoglycemic35526 An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
LipolyticAn agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Quinone-reductase inducerAn agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
alliaceous
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
onion
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
garlic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
metallic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.