Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:09:52 UTC |
---|
Update date | 2019-11-26 03:05:36 UTC |
---|
Primary ID | FDB011861 |
---|
Secondary Accession Numbers | Not 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 Number | 555-66-8 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one, 9ci | HMDB | 1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one, 9CI | db_source | 4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)- | biospider | Shogaol | db_source |
|
---|
Predicted Properties | |
---|
Chemical Formula | C17H24O3 |
---|
IUPAC name | 1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one |
---|
InChI Identifier | InChI=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 Key | OQWKEEOHDMUXEO-UHFFFAOYSA-N |
---|
Isomeric SMILES | CCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C1 |
---|
Average Molecular Weight | 276.3707 |
---|
Monoisotopic Molecular Weight | 276.172544634 |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Benzenoids |
---|
Class | Phenols |
---|
Sub Class | Methoxyphenols |
---|
Direct Parent | Shogaols |
---|
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 Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Ontology | No ontology term |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | liquid | |
---|
Physical Description | Oil | DFC |
---|
Mass Composition | C 73.88%; H 8.75%; O 17.37% | DFC |
---|
Melting Point | Not Available | |
---|
Boiling Point | Bp2.25 201.3° (Lit. gives a pressure range) | DFC |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
Predicted GC-MS | [8]-Shogaol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-9620000000-f02bcd9c6283a8cf88fc | Spectrum | Predicted GC-MS | [8]-Shogaol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05iu-9154000000-46bfcab1accb3045874c | Spectrum | Predicted GC-MS | [8]-Shogaol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | [8]-Shogaol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-1190000000-06bc9c8afe1085ba2632 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-005i-8950000000-03ec6db458ca2af67e59 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0k96-9510000000-caea94c9bbdf4f66b2e6 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-6ef295bdbca7cf3546e1 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-2890000000-eebd2ec4aab29e15a6d3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-4910000000-cd83ea72d889effd1847 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-04e9fac4b2d89f8de33c | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0079-0910000000-d969ff7bbc61fa67e090 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01c9-7900000000-f0e945b67230d4f40916 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002r-0940000000-7539d94259bc6d6ea4eb | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-5910000000-95c63f7cd49c9953b9a8 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fy9-4900000000-79cdde4da585ea08da9b | 2021-09-25 | View Spectrum |
|
---|
NMR | Not Available |
---|
External Links |
---|
ChemSpider ID | Not Available |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | Not Available |
---|
Pubchem Compound ID | 5281794 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | Not Available |
---|
CRC / DFC (Dictionary of Food Compounds) ID | HBF68-C:OGP05-N |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | SHOGAOL|6-SHOGAOL |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00002774 |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Shogaol |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | HBF68-C:HBF68-C |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
---|
5-lipoxygenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | anti 5-hydroxytryptamine | 48279 | Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists. | DUKE | anti allergic | 50857 | A drug used to treat allergic reactions. | DUKE | anti emetic | 50919 | A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors. | DUKE | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | anti histaminic | 37956 | Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti prostaglandin | 49020 | A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. | DUKE | anti pyretic | 35493 | A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever. | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti tussive | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | DUKE | bradycardic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | cardiodepressant | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | cardiotonic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | central nervous system depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | cyclooxygenase inhibitor | 35544 | A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. | DUKE | enteromotility enhancer | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | gastrostimulant | 55324 | A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion. | DUKE | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | hypertensive | | | DUKE | hypotensive | | | DUKE | larvicide | | | DUKE | molluscicide | 33904 | A substance used to destroy pests of the phylum Mollusca. | DUKE | mutagenic | | | DUKE | nematicide | 25491 | A substance used to destroy pests of the phylum Nematoda (roundworms). | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | pressor | | | DUKE | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | DUKE | sprout inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | sympathomimetic | 35524 | A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. | DUKE | thermogenic | | | DUKE | vasoconstrictor | 50514 | Drug used to cause constriction of the blood vessels. | DUKE |
|
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not 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.
|
---|