Geranylgeraniol | CAS#24034-73-9 | geranylgeranyl pyrophosphate analog | apoptosis inhibitor | growth suppression

MedKoo Cat#: 540157 | Name: Geranylgeraniol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Geranylgeraniol is an geranylgeranyl pyrophosphate analog used in synthesis of vitamins E and K. It induces apoptosis and inhibits growth of various tumor cells, suppresses growth of Mycobacterium, and protects monocytes against statin-induced cytotoxicity.

Chemical Structure

Geranylgeraniol

CAS#24034-73-9

Theoretical Analysis

MedKoo Cat#: 540157

Name: Geranylgeraniol

CAS#: 24034-73-9

Chemical Formula: C20H34O

Exact Mass: 290.2610

Molecular Weight: 290.49

Elemental Analysis: C, 82.69; H, 11.80; O, 5.51

Price and Availability

Size	Price	Availability	Quantity
1g	USD 650.00	2 Weeks
5g	USD 1,250.00	2 Weeks

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Synonym

Geranylgeraniol; Geranyl geraniol; (E,E,E)-Geranylgeraniol; Tetraprenol; trans-Geranylgeraniol; Geranylgeranyl alcohol; GG Alcohol

IUPAC/Chemical Name

(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol

InChi Key

OJISWRZIEWCUBN-QIRCYJPOSA-N

InChi Code

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+

SMILES Code

C/C(C)=C\CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CO

Appearance

Liquid

Purity

> 95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

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.

In vitro activity:

At 48 and 72 h, the addition of GGOH (geranylgeraniol) doses from 0.5 to 25 μM was able to increase the viability of ZA (zoledronic acid)-treated fibroblasts in a dose-dependent manner compared to fibroblasts treated with ZA without GGOH. Three GGOH doses (5, 10, and 25 μM) significantly increased the metabolic activity of cells compared to control levels after 72 h (p < 0.05) (Figure 5A). The increased confluence of fibroblasts in the presence of ZA and GGOH 10 μM is shown in Figure 3D. Reference: Front Oral Health. 2022 Jun 20;3:892615. https://pubmed.ncbi.nlm.nih.gov/35795156/

In vivo activity:

The ZA (zoledronic acid) + GGOH (geranylgeraniol) mouse group demonstrated filling with woven bone with few scattered empty osteocyte lacunae. The percentage of osteonecrotic area was significantly decreased in the ZA + GGOH group compared with that in the ZA group (Figure 4E). Apoptosis could hardly be captured in vehicle sockets (Figure 4F). The prominent ACs concentrated on alveolar crest were observed in extraction sockets after ZA treatment. In contrast, simultaneous injection with GGOH could reduce ACs to a normal level (Figure 4F). All these findings suggest that GGOH rescues the ZA-impaired socket healing and represses osteocytic apoptosis. Reference: Front Cell Dev Biol. 2021 Nov 3;9:770899. https://pubmed.ncbi.nlm.nih.gov/34805177/

Preparing Stock Solutions

The following data is based on the product molecular weight 290.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Rattanawonsakul K, Bullock G, Bolt R, Claeyssens F, Atkins S, Hearnden V. In vitro Effect of Geranylgeraniol (GGOH) on Bisphosphonate-Induced Cytotoxicity of Oral Mucosa Cells. Front Oral Health. 2022 Jun 20;3:892615. doi: 10.3389/froh.2022.892615. PMID: 35795156; PMCID: PMC9251184. 2. Saputra WD, Shono H, Ohsaki Y, Sultana H, Komai M, Shirakawa H. 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. doi: 10.3390/ijms221910543. PMID: 34638882; PMCID: PMC8508820. 3. Chen X, Zhu W, Xu R, Shen X, Fu Y, Cheng J, Liu L, Jiang H. Geranylgeraniol Restores Zoledronic Acid-Induced Efferocytosis Inhibition in Bisphosphonate-Related Osteonecrosis of the Jaw. Front Cell Dev Biol. 2021 Nov 3;9:770899. doi: 10.3389/fcell.2021.770899. PMID: 34805177; PMCID: PMC8595285. 4. Chung E, Elmassry MM, Cao JJ, Kaur G, Dufour JM, Hamood AN, Shen CL. Beneficial effect of dietary geranylgeraniol on glucose homeostasis and bone microstructure in obese mice is associated with suppression of proinflammation and modification of gut microbiome. Nutr Res. 2021 Sep;93:27-37. doi: 10.1016/j.nutres.2021.07.001. Epub 2021 Jul 9. PMID: 34352722; PMCID: PMC8464510.

In vitro protocol:

In vivo protocol:

1. Chen X, Zhu W, Xu R, Shen X, Fu Y, Cheng J, Liu L, Jiang H. Geranylgeraniol Restores Zoledronic Acid-Induced Efferocytosis Inhibition in Bisphosphonate-Related Osteonecrosis of the Jaw. Front Cell Dev Biol. 2021 Nov 3;9:770899. doi: 10.3389/fcell.2021.770899. PMID: 34805177; PMCID: PMC8595285. 2. Chung E, Elmassry MM, Cao JJ, Kaur G, Dufour JM, Hamood AN, Shen CL. Beneficial effect of dietary geranylgeraniol on glucose homeostasis and bone microstructure in obese mice is associated with suppression of proinflammation and modification of gut microbiome. Nutr Res. 2021 Sep;93:27-37. doi: 10.1016/j.nutres.2021.07.001. Epub 2021 Jul 9. PMID: 34352722; PMCID: PMC8464510.

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