8-Gingerol

Names

[ Name ]:
8-Gingerol

[Synonym ]:
8-Gingerol
(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone
3-Dodecanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-
(5s)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one
(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-dodecanone

Biological Activity

[Description]:

8-Gingerol, found in the rhizomes of ginger (Z. officinale) with oral bioavailability, activates TRPV1, with an EC50 of 5.0 µM. 8-Gingerol inhibits COX-2, and inhibits the growth of H. pylori in vitro[1][2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

[References]

[1]. Dedov, V.N., et al. Gingerols: a novel class of vanilloid receptor (VR1) agonists. Br. J. Pharmacol. 137(6), 793-798 (2002).

[2]. Chrubasik, S., et al. Zingiberis rhizoma: A comprehensive review on the ginger effect and efficacy profiles. Phytomedicine 12(9), 684-701 (2005).

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
476.4±35.0 °C at 760 mmHg

[ Melting Point ]:
30 - 32 °C

[ Molecular Formula ]:
C₁₉H₃₀O₄

[ Molecular Weight ]:
322.439

[ Flash Point ]:
162.6±19.4 °C

[ Exact Mass ]:
322.214417

[ PSA ]:
66.76000

[ LogP ]:
3.55

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.517

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
methanol: soluble1mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JR4362000

CHEMICAL NAME :: 3-Dodecanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-(+)-

CAS REGISTRY NUMBER :: 23513-08-8

LAST UPDATED :: 199503

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C19-H30-O4

MOLECULAR WEIGHT :: 322.49

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZYZAEU Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. China) V.24- 1989- Volume(issue)/page/year: 25,231,1990

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317

[ Precautionary Statements ]:
P280

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
43

[ Safety Phrases ]:
36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3.0

[ RTECS ]:
JR4362000

[ HS Code ]:
29145019

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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To determine the reaction kinetics for regioselective glucuronidation of gingerols (i.e. 6-, 8- and 10-gingerol) by human liver microsomes and expressed UDP-glucuronosyltransferase (UGT) enzymes, and ...

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