GERANYLGERANIOL

Product NameGERANYLGERANIOL
CAS24034-73-9
MFC20H34O
MW290.48
EINECS
MOL File24034-73-9.mol

Chemical Properties

Boiling point	152-153 °C(Press: 0.07 Torr)
Density	0.8930 g/cm3(Temp: 18 °C)
storage temp.	-20°C
solubility	Chloroform (Sparingly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
form	liquid
pka	14.42±0.10(Predicted)
color	Colourless to Light Yellow
BRN	1913779
Stability	Light Sensistive, Temperature Sensitive
Cosmetics Ingredients Functions	HUMECTANT ANTIMICROBIAL ANTIOXIDANT
InChI	InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+
InChIKey	OJISWRZIEWCUBN-QIRCYJPOSA-N
SMILES	C(O)/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/C)\C

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
HS Code	29052290
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Light Yellow Oil

Uses

A intermediate in the lipidation of proteins, which plays a great importance for a variety of biological processes such as cell signalling

Uses

Geranylgeraniol, a precursor to Geranylgeranylpyrophosphate (G367600), is an intermediate in the mevalonate pathway. Geranylgeraniol has been shown to prevent bone re-adsorption, inhibition of osteoclast formation, and kinase activation in vitro.

Definition

ChEBI: Geranylgeraniol is a diterpenoid that is hexadeca-2,6,10,14-tetraene substituted by methyl groups at positions 3, 7, 11 and 15 and a hydroxy group at position 1. It has a role as a plant metabolite, a volatile oil component and an antileishmanial agent. It is a diterpenoid and a polyprenol.

Biochem/physiol Actions

As the pyrophosphate, the metabolic precursor of all diterpenes. Screening in vitro shows this to be a potent and selective agent against Mycobacterium tuberculosis.

in vivo

Geranylgeraniol (725 mg/kg/d; p.o.; 90 d) is not toxicologically significant with a dose below 725 mg/kg/d in rats^[3].
Geranylgeraniol (483 mg/kg/d; p.o.; 10 d) suppresses lipopolysaccharide-induced inflammation via inhibition of nuclear factor-κB activation in rats^[4].

Animal Model:	Han Wistar rats (169-192 g for male; 116-152 g for female)^[3]
Dosage:	0, 725, 1450, and 2900 mg/kg
Administration:	Oral gavage; once daily; 90 days
Result:	Showed the lowest observed adverse effect level (LOAEL) for local effects and the no observed adverse effect level (NOAEL) for systemic effects as 725 mg/kg/d. Reduced body weights by 12.9 and 21.6% in the intermediate- and high-dose group males, respectively, compared to controls.

Animal Model:	Wistar rats (male, 8-week-old, 130-150 g)^[4]
Dosage:	0, 48.3, 483, 4830 mg/kg
Administration:	Oral gavage; once daily; 10 days; with or not LPS challenge (i.p.; 0.5 mg/kg)
Result:	Suppressed LPS-induced inflammatory cytokines and mRNA expression of LPS-induced inflammatory genes in liver with doses of 483 mg/kg and 4830 mg/kg. Suppressed protein levels of IRAK1, TRAF6, and TAK1, originating from transcriptional down-regulation with doses of 483 mg/kg and 4830 mg/kg.

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