Gallocatechol
Gallocatechol
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Names |
Other names
(+)-gallocatechin |
Identifiers |
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1617-55-6 Y |
ChEBI |
CHEBI:68330 N |
ChEMBL |
ChEMBL47386 N |
ChemSpider |
58594 N |
InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1 NKey: XMOCLSLCDHWDHP-SWLSCSKDSA-N NInChI=1/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1 Key: XMOCLSLCDHWDHP-SWLSCSKDBQ
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Jmol-3D images |
Image |
MeSH |
Gallocatechol |
PubChem |
65084 |
C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
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Properties |
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C15H14O7 |
Molar mass |
306.267 g/mol |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
N verify (what is: Y/N?) |
Infobox references |
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Gallocatechol or gallocatechin (EGC) is a flavan-3-ol, a type of chemical compound including catechin, with the gallate residue being in an isomeric trans position. It is one of the antioxidant chemicals found in food.
This compound possesses two epimers. The most common, (+)-gallocatechin (GC), CAS number 970-73-0, is found notably in green tea. Other sources of (+)-gallocatechin are bananas,[1] persimmon and pomegranate. The other enantiomer is called (-)-gallocatechin or ent-gallocatechin.
This compound had been shown to have moderate affinity to the human cannabinoid receptor,[2] which may contribute to the health benefits found by consuming green tea.
Epigallocatechin is an other type of catechin, with the gallate residue being in an isomeric cis position. It can be found in St John's wort.[3]
See also
References
- ↑ Antioxidant compounds from bananas (Musa cavendish). S. Someya, Y. Yoshiki and K. Okubo, Food Chemistry, Volume 79, Issue 3, November 2002, pp. 351-354, doi:10.1016/S0308-8146(02)00186-3
- ↑ Korte, G.; Dreiseitel, A.; Schreier, P.; Oehme, A.; Locher, S.; Geiger, S.; Heilmann, J.; Sand, P. (2010). "Tea catechins' affinity for human cannabinoid receptors". Phytomedicine : international journal of phytotherapy and phytopharmacology 17 (1): 19–22. doi:10.1016/j.phymed.2009.10.001. PMID 19897346.
- ↑ Separation of epigallocatechin and flavonoids from Hypericum perforatum L. by high-speed counter-current chromatography and preparative high-performance liquid chromatography. Yun Wei, Qianqian Xie,Wanting Dong and Yoichiro Ito, Journal of Chromatography A, 1216 (2009), pages 4313–4318, doi:10.1016/j.chroma.2008.12.056
External links
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| Flavan-3-ols | |
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| O-methylated flavan-3ols |
- Meciadanol (3-O-methylcatechin)
- Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
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| Glycosides |
- Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside)
- Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside)
- Catechin-3-O-glucoside
- Catechin-3'-O-glucoside
- Catechin-4'-O-glucoside
- Catechin-5-O-glucoside
- Catechin-7-O-glucoside
- (+)-Catechin 7-O-β-D-xylopyranoside
- Epicatechin-3′-O-glucoside
- Glochiflavanoside A, B, C D
- Polydine ((+)-catechin 7-0-α-L-arabinoside)
- Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
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| Acetylated | |
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| Misc. | |
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| Receptor (ligands) | |
- Note: The above list contains only some known CB1R agonists, as too many exist to list here completely. Refer here instead for more.
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- Agonists: 2-AG
- 2-AGE (noladin ether)
- 4-O-Methylhonokiol
- A-796,260
- A-834,735
- A-836,339
- AM-1221
- AM-1235
- AM-1241
- AM-2232
- Anandamide
- AZ-11713908
- Cannabinol
- Caryophyllene
- CBS-0550
- CP-55,940
- GW-405,833 (L-768,242)
- GW-842,166X
- HU-308
- JTE 7-31
- JWH-007
- JWH-015
- JWH-018
- JWH-73
- JWH-133
- L-759,633
- L-759,656
- Magnolol
- MDA-19
- Nabitan
- PF-03550096
- S-444,823
- SER-601
- Serinolamide A
- UR-144
- Tedalinab
- THC (dronabinol)
- THCV
- Tetrahydromagnolol
- Virodhamine
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| Transporter (inhibitors) | |
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| Enzyme (inhibitors) | | |
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- IDFP
- JZL-184
- JZL-195
- URB-602
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| Alcohols | |
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| Barbiturates | |
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| Benzodiazepines | |
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| Carbamates | |
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| Flavonoids | |
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| Imidazoles | |
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| Kavalactones |
- Kava
- Yangonin
- 10-methoxyyangonin
- 11-methoxyyangonin
- 11-hydroxyyangonin
- Desmethoxyyangonin
- 11-methoxy-12-hydroxydehydrokavain
- 7,8-dihydroyangonin
- Kavain
- 5-hydroxykavain
- 5,6-dihydroyangonin
- 7,8-dihydrokavain
- 5,6,7,8-tetrahydroyangonin
- 5,6-dehydromethysticin
- Methysticin
- 7,8-dihydromethysticin
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| Neuroactive steroids | |
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| Nonbenzodiazepines | |
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| Phenols | |
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| Piperidinediones | |
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| Pyrazolopyridines | |
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| Quinazolinones | |
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| Volatiles/gases | |
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| Others/unsorted |
- 3-Hydroxybutanal
- α-EMTBL
- AA-29504
- Avermectins (e.g., ivermectin)
- Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- DEABL
- Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine))
- DS2
- Efavirenz
- Etazepine
- Etifoxine
- Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid)
- Fluoxetine
- Flupirtine
- Hopantenic acid
- Lanthanum
- Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
- Loreclezole
- Menthyl isovalerate (validolum)
- Monastrol
- Niacin
- Nicotinamide (niacinamide)
- Org 25,435
- Phenytoin
- Propanidid
- Retigabine (ezogabine)
- Safranal
- Seproxetine
- Stiripentol
- Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional)
- Terpenoids (e.g., borneol)
- Topiramate
- Valerian constituents (e.g., isovaleric acid, valerenic acid, valerenol)
- Unsorted benzodiazepine site PAMs: MRK-409 (MK-0343)
- TCS-1105
- TCS-1205
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| See also: GABAergics |
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