Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2019-11-26 02:55:55 UTC
Primary IDFDB001108
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-[6]-Gingerol
DescriptionGingerol belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one. Gingerol is a pungent tasting compound. Gingerol is found, on average, in the highest concentration within gingers (Zingiber officinale). Gingerol has also been detected, but not quantified in, several different foods, such as cloves (Syzygium aromaticum), star anises (Illicium verum), ceylon cinnamons (Cinnamomum verum), pepper (spice), and nutmegs (Myristica fragrans). This could make gingerol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Gingerol.
CAS Number58253-27-3
Structure
Thumb
Synonyms
SynonymSource
6g [6]-GingerolChEMBL, HMDB
5-Hydroxy-1-(4-hydroxy-3-methoxtphenyl)-3-decanoneHMDB
5-Hydroxy-1-(4-hydroxy-3-methoxycyclohexyl)decan-3-oneHMDB
6-GingerolHMDB
[6]-GingerolHMDB
(6)-GingerolMeSH, HMDB
10-GingerolMeSH, HMDB
(+)-[6]-Gingerolbiospider
(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-onebiospider
(S)-(+)-[6]-Gingerolbiospider
(S)-(+)-[6]Gingerolbiospider
(S)-6-Gingerolbiospider
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-biospider
5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanonebiospider
Gingerolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP3.45ALOGPS
logP3.62ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity83.11 m³·mol⁻¹ChemAxon
Polarizability33.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H26O4
IUPAC name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
InChI IdentifierInChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3
InChI KeyNLDDIKRKFXEWBK-UHFFFAOYSA-N
Isomeric SMILESCCCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C1
Average Molecular Weight294.3859
Monoisotopic Molecular Weight294.18310932
Classification
Description Belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentGingerols
Alternative Parents
Substituents
  • Gingerol
  • Fatty alcohol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Beta-hydroxy ketone
  • Fatty acyl
  • Ketone
  • Secondary alcohol
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 69.36%; H 8.90%; O 21.74%DFC
Melting Point31 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +26.5 (c, 1 in CHCl3)DFC
Spectroscopic UV Data282 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(S)-[6]-Gingerol, non-derivatized, GC-MS Spectrumsplash10-000i-3910000000-3c07be71d662410144abSpectrum
GC-MS(S)-[6]-Gingerol, non-derivatized, GC-MS Spectrumsplash10-000i-3910000000-3c07be71d662410144abSpectrum
Predicted GC-MS(S)-[6]-Gingerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6900000000-9e3ae5652d5b17b9016dSpectrum
Predicted GC-MS(S)-[6]-Gingerol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7119300000-fbff188e294cacd919c6Spectrum
Predicted GC-MS(S)-[6]-Gingerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0920000000-010ef6242d9f56fa2a722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-36e283e52cb0ba857d0e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-35209ecc08a0fcbe33382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-1900000000-aefaf0623f9721907b4d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00du-6900000000-50259fc38798f28309322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-35209ecc08a0fcbe33382021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-aefaf0623f9721907b4d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-36e283e52cb0ba857d0e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0920000000-010ef6242d9f56fa2a722021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00du-6900000000-50259fc38798f28309322021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0290000000-da571dea1713ff08f13b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4930000000-922f5386fa26a96a1bbc2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9400000000-e27c462b7ff389743a4c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-d356007500cff17f32ac2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-3930000000-be6a576d74a0f97fb8fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5900000000-31f35b868a26cada9bf52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0551-0590000000-d52178d2e2ff78317f7b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-2940000000-060d47dec6b201c1d70d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3900000000-2ea673e61b75d0b2bbe92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-4590000000-b65edb04dc7fdd19e6e32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6890000000-9e209efe1855c3c2ace72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9700000000-cd27d9c02d1d0d56a9542021-09-23View Spectrum
NMRNot Available
ChemSpider ID3354
ChEMBL IDCHEMBL1950582
KEGG Compound IDC10462
Pubchem Compound ID3473
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID648
DrugBank IDNot Available
HMDB IDHMDB05783
CRC / DFC (Dictionary of Food Compounds) IDHCV46-D:BTF04-O
EAFUS IDNot Available
Dr. Duke ID6-GINGEROL|GINGEROL|(+)-6-GINGEROL
BIGG IDNot Available
KNApSAcK IDC00002748
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1384651
SuperScent IDNot Available
Wikipedia IDGingerol
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
AmphitensiveA vasodilator that lowers blood pressure by relaxing blood vessels, while also increasing cardiac output. Its biological role involves improving blood flow and reducing vascular resistance. Therapeutically, it has applications in managing hypertension, heart failure, and angina. Key medical uses include treating cardiovascular diseases and improving exercise tolerance in patients with cardiac conditions.DUKE
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti 5-hydroxytryptamine48279 An agent that blocks the activity of serotonin (5-HT), reducing its effects on various bodily functions. It has therapeutic applications in managing conditions like nausea, vomiting, and migraine headaches, and is commonly used to treat serotonin-related disorders, such as carcinoid syndrome and serotonin syndrome.DUKE
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 emetic50919 An agent that prevents or alleviates nausea and vomiting, playing a crucial role in managing chemotherapy-induced, motion-induced, and post-operative nausea. Therapeutically, it helps reduce discomfort and prevent dehydration, commonly used in oncology, gastroenterology, and anesthesia.DUKE
Anti hepatotoxic62868 An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.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-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 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 pyretic35493 An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.DUKE
Anti schistosomiac33281 An agent that treats schistosomiasis, a parasitic disease caused by Schistosoma worms. It kills or inhibits the growth of these parasites, reducing symptoms and preventing complications. Therapeutically, it is used to manage and prevent schistosomiasis, particularly in tropical and subtropical regions where the disease is prevalent.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 seratogenicAn agent that inhibits serotonin production or activity, reducing its effects on the body. It plays a role in regulating mood, appetite, and sleep. Therapeutically, anti seratogenic agents are used to treat conditions like serotonin syndrome, migraine, and anxiety disorders, as well as manage side effects of certain medications.DUKE
Anti thromboxane35222 An agent that inhibits thromboxane A2, reducing platelet aggregation and blood clot formation. Therapeutically, it prevents thrombosis and is used to manage conditions like coronary artery disease, stroke, and myocardial infarction, as well as to prevent blood clots during surgeries.DUKE
Anti-tussive52217 An agent that suppresses coughing, reducing the frequency and severity of coughs. It works by targeting the brain's cough center, providing therapeutic relief for dry, irritating coughs. Key medical uses include managing coughs associated with colds, flu, and other respiratory conditions.DUKE
Anti ulcer49201 An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.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
Cardiodepressant38070 An agent that slows heart rate and reduces cardiac contractility, used to manage conditions like hypertension, angina, and arrhythmias, reducing the heart's workload and oxygen demand.DUKE
Cardiotonic38070 An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.DUKE
CholagogueAn agent that stimulates the release of bile from the gallbladder, promoting digestion and relieving bile duct issues. Therapeutically, it aids in treating gallstones, jaundice, and liver disorders, while also supporting digestive health.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
DepressorA muscle or nerve that lowers the position of a body part or blood pressure upon contraction or stimulation, playing a role in regulating movement and circulation, with therapeutic applications in managing conditions like hypertension and orthostatic hypotension.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
Gastrostimulant55324 An agent that stimulates digestive motility, increasing gastrointestinal movement and secretion. It enhances gut function, relieving symptoms of gastroparesis, constipation, and other motility disorders, commonly used in managing conditions like diabetes-related gastroparesis and postoperative ileus.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
HypertensiveAn agent that increases blood pressure, used therapeutically to treat hypotension (low blood pressure) and shock, and medically to manage conditions such as orthostatic hypotension and postural hypotension.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
InotropicAn agent that alters the force or energy of muscular contractions, particularly in the heart. It has therapeutic applications in treating heart failure and cardiogenic shock. Positively inotropic agents, such as digoxin, increase contraction strength, while negatively inotropic agents, like beta blockers, weaken it, commonly used to manage arrhythmias and hypertension.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
Molluscicide33904 An agent that kills mollusks, particularly snails and slugs, playing a key role in controlling vectors of parasitic diseases. Therapeutically, it is used to prevent the spread of schistosomiasis and other snail-borne diseases, with medical applications in public health and epidemiology.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.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 synthesis inhibitor35222 An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs).DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
ThermogenicAn agent that increases heat production through metabolic stimulation, used to enhance weight loss, improve insulin sensitivity, and treat conditions like hypothyroidism and obesity, by stimulating metabolism and energy expenditure.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
pungent
  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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— 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.