Record Information
Version1.0
Creation date2010-04-08 22:09:45 UTC
Update date2019-11-26 03:05:10 UTC
Primary IDFDB011636
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAjoene
DescriptionIsolated from garlic (Allium sativum) extracts. Nutriceutical with anti-cancer props. Ajoene (pronounced /???ho?i?n/) is a chemical compound available from garlic (Allium sativum). The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of two isomers, E-, and Z- 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.; Ajoene, an unsaturated disulfide, is formed from the bonding of three allicin molecules. Allicin is a sulfinyl compound that gives garlic its strong odor and flavor. The release of allicin occurs after a garlic clove is crushed or finely chopped. Subsequent formation of ajoene occurs when allicin is dissolved in various solvents including edible oils. Ajoene is also found in garlic extract. Ajoene is most stable and most abundant in macerate of garlic (chopped garlic in edible oil).
CAS Number92285-01-3
Structure
Thumb
Synonyms
SynonymSource
2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9CIdb_source
2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfidebiospider
4,5,9-Trithia-1,6,11-dodecatriene 9-oxidedb_source
4,5,9-Trithiadodeca-1,6,11-triene 9-oxidebiospider
Ajoene, trans-biospider
Allyl 3-allylsulfinyl-1-propenyl disulfidedb_source
Disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenylbiospider
Trans-ajoenebiospider
Predicted Properties
PropertyValueSource
logP1.66ChemAxon
pKa (Strongest Acidic)14.9ChemAxon
pKa (Strongest Basic)-8.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69 m³·mol⁻¹ChemAxon
Polarizability25.3 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H14OS3
IUPAC name3-{[(1Z)-3-[(S)-prop-2-ene-1-sulfinyl]prop-1-en-1-yl]disulfanyl}prop-1-ene
InChI IdentifierInChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5-
InChI KeyIXELFRRANAOWSF-ALCCZGGFSA-N
Isomeric SMILESC=CCSS\C=C/CS(=O)CC=C
Average Molecular Weight234.402
Monoisotopic Molecular Weight234.02067714
Classification
Description Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfoxides
Sub ClassNot Available
Direct ParentSulfoxides
Alternative Parents
Substituents
  • Allyl sulfur compound
  • Sulfoxide
  • Organic disulfide
  • Sulfenyl compound
  • Sulfinyl compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 46.12%; H 6.02%; O 6.83%; S 41.04%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 240 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID8056824
ChEMBL IDNot Available
KEGG Compound IDC16757
Pubchem Compound ID9881148
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33566
CRC / DFC (Dictionary of Food Compounds) IDGWS23-E:GWS23-E
EAFUS IDNot Available
Dr. Duke IDTRANS-AJOENE|TRANS-CIS-AJOENE|AJOENE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAjoene
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
Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.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-herpetic22587 An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.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-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti leukotriene35222 An agent that blocks the action of leukotrienes, reducing inflammation and bronchoconstriction. Therapeutically, it is used to treat asthma, allergic rhinitis, and other respiratory disorders by inhibiting the biological role of leukotrienes in mediating inflammatory responses.DUKE
Anti-lymphomicAn agent that targets and destroys lymphatic cells that form tumors, playing a crucial role in cancer treatment. Therapeutically, it is used to manage lymphomas, with key medical applications in chemotherapy and immunotherapy to combat blood cell cancers.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti metastatic35610 An agent that inhibits cancer cell spread, reducing tumor metastasis. It plays a biological role in blocking cell migration and invasion, and has therapeutic applications in cancer treatment. Key medical uses include preventing cancer recurrence and improving survival rates in patients with various types of cancer.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti mycoticAn agent that destroys or prevents the growth of fungi, playing a crucial role in treating fungal infections. Therapeutically, it is used to manage conditions such as athlete's foot, ringworm, and candidiasis, and has key medical applications in dermatology and immunocompromised patient care.DUKE
Anti plateletAn agent that prevents blood clot formation by inhibiting platelet aggregation, used to treat and prevent heart disease, stroke, and other cardiovascular conditions.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.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
Anti-stomatiticAn agent that relieves inflammation of the mucous membrane of the mouth, reducing oral discomfort and pain. Its biological role is to soothe and protect the mucosa, with therapeutic applications in managing mouth ulcers, oral thrush, and other stomatitis-related conditions. Key medical uses include treating oral inflammation, irritation, and infections.DUKE
Anti thrombotic50248 An agent that prevents blood clot formation, reducing the risk of thrombosis. Its biological role is to inhibit platelet aggregation and blood coagulation. Therapeutically, it is used to prevent and treat conditions such as stroke, heart attack, and deep vein thrombosis, as well as to manage atrial fibrillation and peripheral artery disease.DUKE
Anti trypanosomic33281 An agent that targets and eliminates trypanosomes, parasites causing diseases like sleeping sickness and Chagas disease. It plays a crucial role in treating and preventing these diseases, with therapeutic applications in tropical medicine and key medical uses in treating parasitic infections.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
ApoptoticAn agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
CandidicideAn agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.DUKE
CandidistatAn antifungal agent that inhibits the growth of Candida species, such as Candida albicans, used to treat fungal infections, particularly candidiasis.DUKE
Cyclooxygenase-2 inhibitor50629 An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs.DUKE
Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.DUKE
CytostaticAn agent that inhibits cell growth, playing a biological role in regulating cell proliferation. Therapeutically, it is used to slow or stop the growth of abnormal cells. Key medical uses include cancer treatment, where it helps prevent tumor growth, and in managing conditions like psoriasis and rheumatoid arthritis.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
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
FungistatAn agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients.DUKE
Gram(+)icide33282 An agent that targets and kills Gram-positive bacteria, playing a crucial role in treating bacterial infections. Therapeutically, it is used to combat infections caused by Gram-positive microorganisms, with key medical applications including treating skin infections, pneumonia, and sepsis.DUKE
Gram(-)icide33282 An agent that kills Gram-negative bacteria, playing a crucial role in treating infections. Therapeutically, it is used to combat bacterial infections, particularly those resistant to other antibiotics. Key medical uses include treating sepsis, pneumonia, and urinary tract infections caused by Gram-negative bacteria.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
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
Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.DUKE
NF-kappa-B inducerAn agent that stimulates NF-kappa-B, a protein complex regulating DNA transcription, cytokine production, and cell survival, with potential therapeutic applications in inflammation, immune response, and cancer treatment.DUKE
Nitric-oxide inhibitor35222 An agent that blocks the production of nitric oxide, reducing inflammation and vascular relaxation. Therapeutically, it's used to treat conditions like hypertension, angina, and septic shock, by constricting blood vessels and improving blood pressure. Key medical uses include cardiovascular and critical care applications.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
Prostaglandin inhibitor49023 An agent that blocks the production or action of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, by decreasing prostaglandin-mediated responses, providing relief from symptoms.DUKE
Prostaglandin-synthetase inhibitor23924 An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, menstrual cramps, and fever, by inhibiting the enzyme responsible for prostaglandin synthesis, thereby alleviating symptoms.DUKE
ProtisticideAn agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections.DUKE
Antifungal agent52217 Tineacide is an antifungal medication that inhibits fungal growth, commonly used to treat fungal infections such as ringworm, athlete's foot, and jock itch, promoting healthy skin and nail recovery.DUKE
TrypanocideAn agent that kills trypanosomes, used to treat diseases like African sleeping sickness and Chagas disease, caused by Trypanosoma parasites, reducing parasitic infections and associated symptoms.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).