Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2019-11-26 03:05:36 UTC
Primary IDFDB011861
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name[6]-Shogaol
Description[8]-Shogaol belongs to the class of organic compounds known as shogaols. These are ginger derivatives containing a shogaol moiety, which consists of a benzene ring bearing a dec-4-en-3-one moiety, a methoxyphenyl group, a hydroxyl group and at positions 1, 3, and 4, respectively. [8]-Shogaol is found, on average, in the highest concentration within gingers (Zingiber officinale). [8]-Shogaol has also been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make [8]-shogaol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on [8]-Shogaol.
CAS Number555-66-8
Structure
Thumb
Synonyms
SynonymSource
1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one, 9ciHMDB
1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one, 9CIdb_source
4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-biospider
Shogaoldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0089 g/LALOGPS
logP4.95ALOGPS
logP4.85ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity82.69 m³·mol⁻¹ChemAxon
Polarizability32.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H24O3
IUPAC name1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
InChI IdentifierInChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3
InChI KeyOQWKEEOHDMUXEO-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C1
Average Molecular Weight276.3707
Monoisotopic Molecular Weight276.172544634
Classification
Description Belongs to the class of organic compounds known as shogaols. These are ginger derivatives containing a shogaol moiety, which consists of a benzene ring bearing a dec-4-en-3-one moiety, a methoxyphenyl group, a hydroxyl group and at positions 1, 3, and 4, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentShogaols
Alternative Parents
Substituents
  • Shogaol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateliquid
Physical DescriptionOilDFC
Mass CompositionC 73.88%; H 8.75%; O 17.37%DFC
Melting PointNot Available
Boiling PointBp2.25 201.3° (Lit. gives a pressure range)DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS[8]-Shogaol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-9620000000-f02bcd9c6283a8cf88fcSpectrum
Predicted GC-MS[8]-Shogaol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05iu-9154000000-46bfcab1accb3045874cSpectrum
Predicted GC-MS[8]-Shogaol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS[8]-Shogaol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1190000000-06bc9c8afe1085ba26322016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005i-8950000000-03ec6db458ca2af67e592016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9510000000-caea94c9bbdf4f66b2e62016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-6ef295bdbca7cf3546e12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2890000000-eebd2ec4aab29e15a6d32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4910000000-cd83ea72d889effd18472016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-04e9fac4b2d89f8de33c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0910000000-d969ff7bbc61fa67e0902021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01c9-7900000000-f0e945b67230d4f409162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0940000000-7539d94259bc6d6ea4eb2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-5910000000-95c63f7cd49c9953b9a82021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fy9-4900000000-79cdde4da585ea08da9b2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5281794
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBF68-C:OGP05-N
EAFUS IDNot Available
Dr. Duke IDSHOGAOL|6-SHOGAOL
BIGG IDNot Available
KNApSAcK IDC00002774
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDShogaol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSHBF68-C:HBF68-C
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-lipoxygenase inhibitor23924 An agent that blocks the activity of 5-lipoxygenase, an enzyme involved in leukotriene production, reducing inflammation and allergic responses. Therapeutically, it's used to treat asthma, allergies, and inflammatory disorders, such as arthritis, by inhibiting the synthesis of pro-inflammatory leukotrienes.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-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 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-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.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
Bradycardic38070 An agent that slows heart rate, reducing cardiac workload. Its biological role is to regulate heart function, and it has therapeutic applications in managing cardiac conditions. Key medical uses include treating tachycardia, arrhythmias, and heart failure, as well as controlling blood pressure and reducing myocardial oxygen demand.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
Central nervous system depressant35470 An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.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
Enteromotility enhancerAn agent that stimulates movement of food through the intestine, enhancing gastrointestinal motility. It has therapeutic applications in treating gastrointestinal disorders, such as constipation and gastroparesis, and is used to manage symptoms of irritable bowel syndrome and other motility-related conditions.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
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
PressorAn agent that increases blood pressure by stimulating constriction of blood vessels, used therapeutically to treat hypotension, shock, and anaphylaxis, and medically to maintain blood pressure during surgery and trauma.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
Sprout inhibitor35222 A plant growth regulator that suppresses seed germination and sprouting, used to extend shelf life of stored potatoes and other tubers. Therapeutically, it has applications in cancer treatment, inhibiting angiogenesis and tumor growth. Key medical uses include anti-cancer and anti-angiogenic therapies.DUKE
Sympathomimetic35524 An agent that mimics the effects of the sympathetic nervous system, increasing heart rate, blood pressure, and energy. Therapeutically, it's used to treat conditions like asthma, hypotension, and shock, as well as nasal decongestion and eye dilation.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
Vasoconstrictor50514 An agent that narrows blood vessels, reducing blood flow. It plays a biological role in regulating blood pressure and is therapeutically used to treat conditions like hypotension, nasal congestion, and bleeding. Key medical uses include managing shock, reducing bleeding during surgery, and relieving migraine headaches.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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.