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Germacrone

CAS No.
6902-91-6
Chemical Name:
Germacrone
Synonyms
Germacron;3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (E,E)-;3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (3E,7E)-;GERMACRONE;GERMACRONE(RG);GerMacrol (obsol;(E,E)-GerMacrone;(E,E)-Germacra-3,7(11),9-trien-6-one;Germacra-3,7(11),9-trien-6-one, (E,E)-;Germacrone, 98%, from Curcuma zedoaria (Christm.) Rosc
CBNumber:
CB1497650
Molecular Formula:
C15H22O
Molecular Weight:
218.33
MDL Number:
MFCD00210050
MOL File:
6902-91-6.mol
MSDS File:
SDS
Last updated:2023-06-08 09:03:01

Germacrone Properties

Melting point 55-58 °C
Boiling point 153-157 °C(Press: 13 Torr)
Density 0.9908 g/cm3
storage temp. 2-8°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form Solid
color White to Off-White
λmax 309nm(MeOH)(lit.)
BRN 2047453
Stability Light Sensitive
LogP 4.760 (est)
CAS DataBase Reference 6902-91-6
FDA UNII E2WQ6N4FBP
NIST Chemistry Reference 3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (e,e)-(6902-91-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P280-P305+P351+P338-P337+P313
Safety Statements  23-24/25
RTECS  GU2210000
HS Code  29142990
NFPA 704
0
2 0

Germacrone price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHL89677 Germacrone phyproof? Reference Substance 6902-91-6 10MG $522 2024-03-01 Buy
Sigma-Aldrich 42924 Germacrone ≥95.0% (HPLC) 6902-91-6 10mg $897 2022-05-15 Buy
TCI Chemical G0519 Germacrone >98.0%(GC) 6902-91-6 20mg $178 2024-03-01 Buy
TCI Chemical G0519 Germacrone >98.0%(GC) 6902-91-6 100mg $532 2024-03-01 Buy
Cayman Chemical 30111 Germacrone 6902-91-6 5mg $68 2024-03-01 Buy
Product number Packaging Price Buy
PHL89677 10MG $522 Buy
42924 10mg $897 Buy
G0519 20mg $178 Buy
G0519 100mg $532 Buy
30111 5mg $68 Buy

Germacrone Chemical Properties,Uses,Production

Description

Germacrone is a sesquiterpene that has been found in gingeraceae plants and has diverse biological activities. It inhibits pseudorabies virus (PRV) replication in Vero cells when used at concentrations ranging from 10 to 150 μM. Germacrone (50-250 μM) enhances cytotoxicity and apoptosis induced by doxorubicin in doxorubicin-resistant MCF-7/adr cells. In vivo, germacrone (5, 10, and 20 mg/kg) reduces body weight gain, visceral fat pad weight, serum insulin and plasma glucose levels, and hepatic lipid levels in a mouse model of high-fat diet-induced obesity. It decreases brain malondialdehyde (MDA) levels and activity of superoxide dismutase (SOD) and glutathione peroxidase (GPX), as well as reduces infarct volume in a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).

Uses

Germacrone is an antiviral isolate of Geranium macrorrhizum which inhibits and prevents early stage influenza virus infection. It also inhibits the proliferation of glioma cells by promoting apoptosis.

Definition

ChEBI: (E,E)-germacrone is a germacrane sesquiterpenoid that has formula C15H22O. It is a natural product found in traditional medicinal plants of the family Zingiberaceae. The compound exhibits a range of pharmacological activities including anti-inflammatory, anticancer, antiviral, anti-androgenic, antioxidant, antimicrobial, antifungal, neuroprotective and insecticidal activities. It has a role as a volatile oil component, an antiviral agent, an insecticide, an anti-inflammatory agent, an antioxidant, an antineoplastic agent, an apoptosis inducer, an autophagy inducer, an antimicrobial agent, an androgen antagonist, a neuroprotective agent, a plant metabolite, an antifungal agent, an antitussive, an antifeedant and a hepatoprotective agent. It is a germacrane sesquiterpenoid and an olefinic compound.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 3489, 1983 DOI: 10.1016/S0040-4039(00)86020-7

Hazard

A poison by ingestion

Safety Profile

A poison by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.

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View Lastest Price from Germacrone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Germacrone pictures 2023-02-24 Germacrone
6902-91-6
US $0.00 / mg 5mg ≥98%(HPLC) 10 g Shanghai Standard Technology Co., Ltd.
(3Z,7Z)-3,7-Dimethyl-10-propan-2-ylidene-cyclodeca-3,7-dien-1-one pictures 2019-07-06 (3Z,7Z)-3,7-Dimethyl-10-propan-2-ylidene-cyclodeca-3,7-dien-1-one
6902-91-6
US $1.00 / kg 1g 99% 100KG Career Henan Chemical Co
  • Germacrone pictures
  • Germacrone
    6902-91-6
  • US $0.00 / mg
  • ≥98%(HPLC)
  • Shanghai Standard Technology Co., Ltd.

Germacrone Spectrum

(E,E)-Germacra-3,7(11),9-trien-6-one (E,E)-3,7-Dimethyl-10-(1-methylethylidene)-3,7-cyclodecadien-1-one 3,7-Dimethyl-10-(1-methylethylidene)-3,7-cyclodecadien-1-one Germacra-3,7(11),9-trien-6-one, (E,E)- trans,trans-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one (3E,7E)-3,7-Dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one GERMACRONE(RG) GERMACRONE (3E,7E)-10-Isopropylidene-3,7-diMethyl-3,7-cyclodecadien-1-one (3E,7E)-3,7-DiMethyl-10-(propan-2-ylidene)cyclodeca-3,7-dienone GerMacrol (obsol (E,E)-GerMacrone (3z,7z)-3,7-dimethyl-10-propan-2-ylidene-cyclodeca-3,7-dien-1-one (3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one Germacrone, 98%, from Curcuma zedoaria (Christm.) Rosc 3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (E,E)- Germacron 3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (3E,7E)- (3E, 7E) -3,7-dimethyl-10- (propyl-2-ylidene) cyclodecane-3,7-dien-1-one 6902-91-6 chemical reagent pharmaceutical intermediate phytochemical reference standards from Chinese medicinal herbs (TCM). standardized herbal extract Inhibitors