Geranylgeraniol
featured

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

MedKoo CAT#: 540157

CAS#: 24034-73-9

Description: 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

img
Geranylgeraniol
CAS# 24034-73-9

Theoretical Analysis

MedKoo Cat#: 540157
Name: Geranylgeraniol
CAS#: 24034-73-9
Chemical Formula: C20H34O
Exact Mass: 290.26
Molecular Weight: 290.491
Elemental Analysis: C, 82.69; H, 11.80; O, 5.51

Price and Availability

Size Price Availability Quantity
250mg USD 450 2 Weeks
500mg USD 750 2 Weeks
1g USD 950 2 Weeks
2g USD 1650 2 Weeks
5g USD 2950 2 Weeks
Bulk inquiry

Synonym: Tetraprenol; CJ-24095; CJ24095; CJ 24095; FT-0626663; FT0626663; FT 0626663; Geranylgeraniol

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: Solid powder

Purity: >98% (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:
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.

Recalculate based on batch purity %
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: 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.
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.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Schumacher MM, Elsabrouty R, Seemann J, Jo Y, DeBose-Boyd RA. The prenyltransferase UBIAD1 is the target of geranylgeraniol in degradation of HMG CoA reductase. Elife. 2015 Mar 5;4. doi: 10.7554/eLife.05560. PubMed PMID: 25742604; PubMed Central PMCID: PMC4374513.

2: Fernandes NV, Yeganehjoo H, Katuru R, DeBose-Boyd RA, Morris LL, Michon R, Yu ZL, Mo H. Geranylgeraniol suppresses the viability of human DU145 prostate carcinoma cells and the level of HMG CoA reductase. Exp Biol Med (Maywood). 2013 Nov 1;238(11):1265-74. doi: 10.1177/1535370213492693. Epub 2013 Sep 4. PubMed PMID: 24006306; PubMed Central PMCID: PMC4010193.

3: Zafar S, Coates DE, Cullinan MP, Drummond BK, Milne T, Seymour GJ. Zoledronic acid and geranylgeraniol regulate cellular behaviour and angiogenic gene expression in human gingival fibroblasts. J Oral Pathol Med. 2014 Oct;43(9):711-21. doi: 10.1111/jop.12181. Epub 2014 Apr 25. PubMed PMID: 24762323.

4: Pabst AM, Krüger M, Ziebart T, Jacobs C, Walter C. Isoprenoid geranylgeraniol: the influence on cell characteristics of endothelial progenitor cells after bisphosphonate therapy in vitro. Clin Oral Investig. 2015 Sep;19(7):1625-33. doi: 10.1007/s00784-014-1394-z. Epub 2015 Jan 16. PubMed PMID: 25589370.

5: You LF, Guo LQ, Lin JF, Ren T, Wang JR. Overproduction of geranylgeraniol in Coprinopsis cinerea by the expression of geranylgeranyl diphosphate synthase gene. J Basic Microbiol. 2014 Dec;54(12):1387-94. doi: 10.1002/jobm.201400152. Epub 2014 Aug 19. PubMed PMID: 25138463.

6: Pabst AM, Krüger M, Ziebart T, Jacobs C, Sagheb K, Walter C. The influence of geranylgeraniol on human oral keratinocytes after bisphosphonate treatment: An in vitro study. J Craniomaxillofac Surg. 2015 Jun;43(5):688-95. doi: 10.1016/j.jcms.2015.03.014. Epub 2015 Mar 27. PubMed PMID: 25913629.

7: Kim J, Lee JN, Ye J, Hao R, Debose-Boyd R, Ye J. Sufficient production of geranylgeraniol is required to maintain endotoxin tolerance in macrophages. J Lipid Res. 2013 Dec;54(12):3430-7. doi: 10.1194/jlr.M042549. Epub 2013 Sep 23. PubMed PMID: 24062519; PubMed Central PMCID: PMC3826689.

8: Katuru R, Fernandes NV, Elfakhani M, Dutta D, Mills N, Hynds DL, King C, Mo H. Mevalonate depletion mediates the suppressive impact of geranylgeraniol on murine B16 melanoma cells. Exp Biol Med (Maywood). 2011 May 1;236(5):604-13. doi: 10.1258/ebm.2011.010379. Epub 2011 May 3. PubMed PMID: 21540247.

9: Marcuzzi A, Piscianz E, Zweyer M, Bortul R, Loganes C, Girardelli M, Baj G, Monasta L, Celeghini C. Geranylgeraniol and Neurological Impairment: Involvement of Apoptosis and Mitochondrial Morphology. Int J Mol Sci. 2016 Mar 11;17(3):365. doi: 10.3390/ijms17030365. PubMed PMID: 26978350; PubMed Central PMCID: PMC4813225.

10: Lopes MV, Desoti VC, Caleare Ade O, Ueda-Nakamura T, Silva SO, Nakamura CV. Mitochondria Superoxide Anion Production Contributes to Geranylgeraniol-Induced Death in Leishmania amazonensis. Evid Based Complement Alternat Med. 2012;2012:298320. doi: 10.1155/2012/298320. Epub 2012 Dec 4. PubMed PMID: 23304195; PubMed Central PMCID: PMC3529489.

11: Zafar S, Coates DE, Cullinan MP, Drummond BK, Milne T, Seymour GJ. Effects of zoledronic acid and geranylgeraniol on the cellular behaviour and gene expression of primary human alveolar osteoblasts. Clin Oral Investig. 2016 Nov;20(8):2023-2035. Epub 2016 Jan 22. PubMed PMID: 26795621.

12: Ho HJ, Shirakawa H, Yoshida R, Ito A, Maeda M, Goto T, Komai M. Geranylgeraniol enhances testosterone production via the cAMP/protein kinase A pathway in testis-derived I-10 tumor cells. Biosci Biotechnol Biochem. 2016;80(4):791-7. doi: 10.1080/09168451.2015.1123612. Epub 2016 Jan 13. PubMed PMID: 26757775.

13: Giriwono PE, Shirakawa H, Ohsaki Y, Hata S, Kuriyama H, Sato S, Goto T, Komai M. 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. doi: 10.1007/s00394-012-0429-y. Epub 2012 Jul 31. PubMed PMID: 22847643.

14: Marcuzzi A, Zanin V, Piscianz E, Tricarico PM, Vuch J, Girardelli M, Monasta L, Bianco AM, Crovella S. Lovastatin-induced apoptosis is modulated by geranylgeraniol in a neuroblastoma cell line. Int J Dev Neurosci. 2012 Oct;30(6):451-6. doi: 10.1016/j.ijdevneu.2012.06.002. Epub 2012 Jul 1. PubMed PMID: 22759742.

15: Kotti T, Head DD, McKenna CE, Russell DW. Biphasic requirement for geranylgeraniol in hippocampal long-term potentiation. Proc Natl Acad Sci U S A. 2008 Aug 12;105(32):11394-9. doi: 10.1073/pnas.0805556105. Epub 2008 Aug 6. PubMed PMID: 18685105; PubMed Central PMCID: PMC2516227.

16: Ohnuma S, Watanabe M, Nishino T. Identification and characterization of geranylgeraniol kinase and geranylgeranyl phosphate kinase from the Archaebacterium Sulfolobus acidocaldarius. J Biochem. 1996 Mar;119(3):541-7. PubMed PMID: 8830051.

17: Mitake M, Shidoji Y. Geranylgeraniol oxidase activity involved in oxidative formation of geranylgeranoic acid in human hepatoma cells. Biomed Res. 2012 Feb;33(1):15-24. PubMed PMID: 22361882.

18: Ziebart T, Koch F, Klein MO, Guth J, Adler J, Pabst A, Al-Nawas B, Walter C. Geranylgeraniol - a new potential therapeutic approach to bisphosphonate associated osteonecrosis of the jaw. Oral Oncol. 2011 Mar;47(3):195-201. doi: 10.1016/j.oraloncology.2010.12.003. Epub 2011 Jan 17. PubMed PMID: 21247791.

19: Calixto NO, da Costa e Silva MC, Gayer CR, Coelho MG, Paes MC, Todeschini AR. Antiplatelet activity of geranylgeraniol isolated from Pterodon pubescens fruit oil is mediated by inhibition of cyclooxygenase-1. Planta Med. 2007 May;73(5):480-3. Epub 2007 Apr 18. PubMed PMID: 17443436.

20: Fisher JE, Rogers MJ, Halasy JM, Luckman SP, Hughes DE, Masarachia PJ, Wesolowski G, Russell RG, Rodan GA, Reszka AA. Alendronate mechanism of action: geranylgeraniol, an intermediate in the mevalonate pathway, prevents inhibition of osteoclast formation, bone resorption, and kinase activation in vitro. Proc Natl Acad Sci U S A. 1999 Jan 5;96(1):133-8. PubMed PMID: 9874784; PubMed Central PMCID: PMC15105.