CAS Number24034-73-9
SynonymsMFCD00129083; Geranylgeraniol; (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol; all trans-3,7,11-15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol
Molecular FormulaC20H34O
Molecular Weight290.48
Purity≥85 (GC)%
Density0.88 g/cm3
Boiling Point397.1ºC at 760 mmHg
Appearanceliquid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 24034-73-9 |
| Catalog No. | 2A-9061394 |
| Chinese Name | 香叶基香叶醇 |
| Synonyms | MFCD00129083; Geranylgeraniol; (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol; all trans-3,7,11-15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol |
| Molecular Formula | C20H34O |
| Molecular Weight | 290.48 |
| Purity | ≥85 (GC) |
| Density | 0.88 g/cm3 |
| Boiling Point | 397.1ºC at 760 mmHg |
| Appearance | liquid |
| Storage Condition | -20℃ |
| Application | Geranylgeraniol is an orally active vitamin K2 isoform and an intermediate in the mevalonate pathway. In animal models, geranylgeraniol targets the NF-kB signaling pathway and can reduce LPS-induced m |
| HTC | 2905290000 |
| PubChem ID | 24895120 |
| MDL Number | MFCD00129083 |
| SMILES | C\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO |
| 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+ |
| InChI Key | OJISWRZIEWCUBN-QIRCYJPOSA-N |
| Beilstein/REAXYS | 1913779 |
| NACRES Code | NA.77 |
| UNSPSC | 12352202 |
| Hazard Symbols | transportation |
| MSDS | msds/61394_1_24034_73_9.pdf |
| Bioactivity | Geranylgeraniol is an orally acitve vitamin K2 sub-type, an intermediate of the mevalonate pathway. Geranylgeraniol targets NF-kB signaling pathway and could alleviate LPS-induced microglial inflammation in animal model[1][2][3][4]. Related Catalog Research Areas >> Inflammation/Immunology Target NF-kB[1] In Vitro Geranylgeraniol (0-10 μM; 24 h) dose-dependently suppresses the LPS-induced increase in the mRNA levels of Il-1β, Tnf-α, Il-6, and Cox-2[1]. Geranylgeraniol (10 μM; 24 h) inhibits the phosphorylation of TAK1, IKKα/β, and NF-κB p65 proteins as well as NF-κB nuclear translocation induced by LPS while maintaining IκBα expression[1]. Geranylgeraniol, (50 μM; 24 h) eliminates cell damage caused by Simvastatin (HY-17502) (10 µM) and Mevalonat (10 mM), and reduces the inflammatory marker and the damage of the mitochondria, maintaining its shape and component[2]. Western Blot Analysis[1] Cell Line: MG6 cell Concentration: 0, 1, 10 μM Incubation Time: 24 hours Result: Suppressed by TAK1, IKKα/β, and NF-κB p65 proteins level at 10 μM. RT-PCR[1] Cell Line: MG6 cell Concentration: 10 μM Incubation Time: 0, 6, 12, 24 hours Result: Significantly inhibited pro-inflammatory cytokine Il-1β, Tnf-α, Il-6, and Cox-2 mRNA level. 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. References [1]. Saputra WD, et al. Geranylgeraniol Inhibits Lipopolysaccharide-Induced Inflammation in Mouse-Derived MG6 Microglial Cells via NF-κB Signaling Modulation. Int J Mol Sci. 2021 Sep 29;22(19):10543. [2]. Marcuzzi A, et al. Geranylgeraniol and Neurological Impairment: Involvement of Apoptosis and Mitochondrial Morphology. Int J Mol Sci. 2016 Mar 11;17(3):365. [3]. Preece K, et al. A toxicological evaluation of geranylgeraniol. Regul Toxicol Pharmacol. 2021 Aug;124:104975. [4]. Giriwono PE, et al. Dietary supplementation with geranylgeraniol suppresses lipopolysaccharide-induced inflammation via inhibition of nuclear factor-κB activation in rats. Eur J Nutr. 2013 Apr;52(3):1191-9. Chemical & Physical Properties Density 0.88 g/cm3 Boiling Point 397.1ºC at 760 mmHg Molecular Formula C20H34O Molecular Weight 290.48300 Flash Point 128.3ºC Exact Mass 290.26100 PSA 20.23000 LogP 6.12440 Vapour Pressure 0mmHg at 25°C Index of Refraction 1.492 InChIKey OJISWRZIEWCUBN-QIRCYJPOSA-N SMILES CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO Storage condition -20°C |
| Use of | Geranylgeraniol is an orally acitve vitamin K2 sub-type, an intermediate of the mevalonate pathway. Geranylgeraniol targets NF-kB signaling pathway and could alleviate LPS-induced microglial inflammation in animal model[1][2][3][4]. Properties Articles46 Name (E,E,E)-geranylgeraniol Synonym More Synonyms GERANYLGERANIOL Biological Activity Description Geranylgeraniol is an orally acitve vitamin K2 sub-type, an intermediate of the mevalonate pathway. Geranylgeraniol targets NF-kB signaling pathway and could alleviate LPS-induced microglial inflammation in animal model[1][2][3][4]. Related Catalog Research Areas >> Inflammation/Immunology References [1]. Saputra WD, et al. Geranylgeraniol Inhibits Lipopolysaccharide-Induced Inflammation in Mouse-Derived MG6 Microglial Cells via NF-κB Signaling Modulation. Int J Mol Sci. 2021 Sep 29;22(19):10543. [2]. Marcuzzi A, et al. Geranylgeraniol and Neurological Impairment: Involvement of Apoptosis and Mitochondrial Morphology. Int J Mol Sci. 2016 Mar 11;17(3):365. [3]. Preece K, et al. A toxicological evaluation of geranylgeraniol. Regul Toxicol Pharmacol. 2021 Aug;124:104975. [4]. Giriwono PE, et al. Dietary supplementation with geranylgeraniol suppresses lipopolysaccharide-induced inflammation via inhibition of nuclear factor-κB activation in rats. Eur J Nutr. 2013 Apr;52(3):1191-9. Chemical & Physical Properties Molecular Formula C20H34O Exact Mass 290.26100 PSA 20.23000 LogP 6.12440 Index of Refraction 1.492 InChIKey OJISWRZIEWCUBN-QIRCYJPOSA-N SMILES CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO |
| Tax Rebate | 9.0% |
| Supervision | none |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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