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MedKoo Cat#: 146226 | Name: Germanicol

Description:

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

Germanicol is a naturally occurring pentacyclic triterpenoid found in various medicinal plants, particularly in the families Lamiaceae and Oleaceae. It exhibits a range of biological activities, including anti-inflammatory, antioxidant, antimicrobial, and anticancer effects. The mechanism of action is believed to involve inhibition of pro-inflammatory enzymes (like COX and LOX), modulation of oxidative stress pathways, and induction of apoptosis in cancer cells through mitochondrial disruption. Due to its pharmacological potential, germanicol is being explored as a lead compound in the development of plant-based therapeutics.

Chemical Structure

Germanicol
Germanicol
CAS#465-02-1

Theoretical Analysis

MedKoo Cat#: 146226

Name: Germanicol

CAS#: 465-02-1

Chemical Formula: C30H50O

Exact Mass: 426.3862

Molecular Weight: 426.73

Elemental Analysis: C, 84.44; H, 11.81; O, 3.75

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Germanicol;
IUPAC/Chemical Name
(3S,4aR,6aR,6bR,8aR,12bS,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12b,13,14,14a,14b-icosahydropicen-3-ol
InChi Key
QMUXVPRGNJLGRT-PNTWTTAKSA-N
InChi Code
1S/C30H50O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h19-20,22-24,31H,9-18H2,1-8H3/t20-,22+,23-,24+,27-,28+,29-,30-/m1/s1
SMILES Code
CC1(C)CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)C2=C1
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 426.73 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
1: Hu YL, Wang XB, Chen DD, Guo XJ, Yang QJ, Dong LH, Cheng L. Germanicol induces selective growth inhibitory effects in human colon HCT-116 and HT29 cancer cells through induction of apoptosis, cell cycle arrest and inhibition of cell migration. J BUON. 2016 May-Jun;21(3):626-32. PMID: 27569083. 2: Ragasa CY, Espineli DL, Shen CC. New triterpenes from Barringtonia asiatica. Chem Pharm Bull (Tokyo). 2011;59(6):778-82. doi: 10.1248/cpb.59.778. PMID: 21628919. 3: Surendra K, Corey EJ. Rapid and enantioselective synthetic approaches to germanicol and other pentacyclic triterpenes. J Am Chem Soc. 2008 Jul 9;130(27):8865-9. doi: 10.1021/ja802730a. PMID: 18597440. 4: Luz LEC, Kanunfre CC, Paludo KS, da Silva Justo A, Petry VK, Lemes BM, Barison A, Nepel A, Wang M, Avula B, Khan IA, Beltrame FL. Cytotoxic biomonitored study of Euphorbia umbellata (Pax) Bruyns. J Ethnopharmacol. 2016 May 13;183:29-37. doi: 10.1016/j.jep.2016.02.025. Epub 2016 Feb 22. PMID: 26906968. 5: Mourão Mulvaney LC, Xavier-Júnior FH, Rodrigues AMS, Stien D, Allegretti SM, Garcia VL. Antimicrobial and anthelmintic activities of the ethanolic extract, fractions and isolated compounds from Manilkara zapota L. P. Royen (Sapotaceae). J Pharm Pharmacol. 2021 Mar 6;73(3):377-387. doi: 10.1093/jpp/rgaa030. PMID: 33793883. 6: Martins V, Szakiel A, Teixeira A, Abdallah C, Moreira C, Pączkowski C, Lanoue A, Gerós H. Combined omics approaches expose metabolite-microbiota correlations in grape berries of three cultivars of Douro wine region. Food Chem. 2023 Dec 15;429:136859. doi: 10.1016/j.foodchem.2023.136859. Epub 2023 Jul 13. PMID: 37463536. 7: Padilha MM, Vilela FC, Rocha CQ, Dias MJ, Soncini R, dos Santos MH, Alves-da- Silva G, Giusti-Paiva A. Antiinflammatory properties of Morus nigra leaves. Phytother Res. 2010 Oct;24(10):1496-500. doi: 10.1002/ptr.3134. PMID: 20878700. 8: Ragasa CY, Espineli DL, Shen CC. A new triterpene from Barringtonia asiatica. Nat Prod Res. 2012;26(20):1869-75. doi: 10.1080/14786419.2011.619187. Epub 2011 Sep 19. PMID: 21929282. 9: Kemboi D, Langat MK, Siwe-Noundou X, Krause RWM, Isaacs ML, Tembu VJ. In vitro antibacterial and cytotoxic effects of Euphorbia grandicornis Blanc chemical constituents. BMC Complement Med Ther. 2022 Mar 25;22(1):90. doi: 10.1186/s12906-022-03571-8. PMID: 35337309; PMCID: PMC8957186. 10: Pereira H, Simões R, Miranda I. Cuticular Waxes and Cutin in Terminalia catappa Leaves from the Equatorial São Tomé and Príncipe Islands. Molecules. 2023 Aug 31;28(17):6365. doi: 10.3390/molecules28176365. PMID: 37687194; PMCID: PMC10489119. 11: Alqasoumi SI, Basudan OA, Al-Rehaily AJ, Abdel-Kader MS. Phytochemical and pharmacological study of Ficus palmata growing in Saudi Arabia. Saudi Pharm J. 2014 Nov;22(5):460-71. doi: 10.1016/j.jsps.2013.12.010. Epub 2013 Dec 25. PMID: 25473335; PMCID: PMC4246364. 12: Srisawat P, Yasumoto S, Fukushima EO, Robertlee J, Seki H, Muranaka T. Production of the bioactive plant-derived triterpenoid morolic acid in engineered Saccharomyces cerevisiae. Biotechnol Bioeng. 2020 Jul;117(7):2198-2208. doi: 10.1002/bit.27357. Epub 2020 May 8. PMID: 32311084. 13: Andre CM, Legay S, Deleruelle A, Nieuwenhuizen N, Punter M, Brendolise C, Cooney JM, Lateur M, Hausman JF, Larondelle Y, Laing WA. Multifunctional oxidosqualene cyclases and cytochrome P450 involved in the biosynthesis of apple fruit triterpenic acids. New Phytol. 2016 Sep;211(4):1279-94. doi: 10.1111/nph.13996. Epub 2016 May 23. PMID: 27214242; PMCID: PMC5089662. 14: Kim DK, Lim JP, Kim JW, Park HW, Eun JS. Antitumor and antiinflammatory constituents from Celtis sinensis. Arch Pharm Res. 2005 Jan;28(1):39-43. doi: 10.1007/BF02975133. PMID: 15742806. 15: Al Musayeib NM, Mothana RA, Ibrahim SR, El Gamal AA, Al-Massarani SM. Klodorone A and klodorol A: new triterpenes from Kleinia odora. Nat Prod Res. 2014;28(15):1142-6. doi: 10.1080/14786419.2014.915831. Epub 2014 May 15. PMID: 24831019. 16: Szakiel A, Niżyński B, Pączkowski C. Triterpenoid profile of flower and leaf cuticular waxes of heather Calluna vulgaris. Nat Prod Res. 2013 Aug;27(15):1404-7. doi: 10.1080/14786419.2012.742083. Epub 2012 Nov 13. PMID: 23148482. 17: Silva CA, Madureira LA. Source correlation of biomarkers in a mangrove ecosystem on Santa Catarina Island in southern Brazil. An Acad Bras Cienc. 2012 Sep;84(3):589-604. doi: 10.1590/s0001-37652012005000042. Epub 2012 Jul 10. PMID: 22782538. 18: da Silva UP, Furlani GM, Demuner AJ, da Silva OLM, Varejão EVV. Allelopathic activity and chemical constituents of extracts from roots of Euphorbia heterophylla L. Nat Prod Res. 2019 Sep;33(18):2681-2684. doi: 10.1080/14786419.2018.1460829. Epub 2018 Apr 9. PMID: 29629832. 19: Srisawat P, Fukushima EO, Yasumoto S, Robertlee J, Suzuki H, Seki H, Muranaka T. Identification of oxidosqualene cyclases from the medicinal legume tree Bauhinia forficata: a step toward discovering preponderant α-amyrin- producing activity. New Phytol. 2019 Oct;224(1):352-366. doi: 10.1111/nph.16013. Epub 2019 Aug 4. PMID: 31230357. 20: Choi HS, Han JY, Cheong EJ, Choi YE. Characterization of a Pentacyclic Triterpene Acetyltransferase Involved in the Biosynthesis of Taraxasterol and ψ-Taraxasterol Acetates in Lettuce. Front Plant Sci. 2022 Jan 3;12:788356. doi: 10.3389/fpls.2021.788356. PMID: 35046976; PMCID: PMC8762322.

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