Hecogenin
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MedKoo CAT#: 584419

CAS#: 467-55-0

Description: Hecogenin is a steroidal sapogenin which has been isolated from plants particularly from numerous Agave species; used in prep of steroidal hormones.


Chemical Structure

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Hecogenin
CAS# 467-55-0

Theoretical Analysis

MedKoo Cat#: 584419
Name: Hecogenin
CAS#: 467-55-0
Chemical Formula: C27H42O4
Exact Mass: 430.3083
Molecular Weight: 430.629
Elemental Analysis: C, 75.31; H, 9.83; O, 14.86

Price and Availability

Size Price Availability Quantity
100.0mg USD 182.0 2 Weeks
250.0mg USD 322.0 2 Weeks
1.0g USD 585.0 2 Weeks
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Synonym: Hecogenin; Hocogenin

IUPAC/Chemical Name: (22R,25R)-3beta-Hydroxy-5alpha-spirostan-12-one

InChi Key: QOLRLLFJMZLYQJ-LOBDNJQFSA-N

InChi Code: InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-22,24,28H,5-14H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22+,24+,25+,26-,27-/m1/s1

SMILES Code: [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@@H](C)[C@@]1([C@]34C)[H])C[C@@]3([H])[C@]5([H])CC[C@@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC4=O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 430.629 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

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1: Gama KB, Quintans JS, Antoniolli AR, Quintans-Júnior LJ, Santana WA, Branco A, Soares MB, Villarreal CF. Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate. J Nat Prod. 2013 Apr 26;76(4):559-63. doi: 10.1021/np3007342. Epub 2013 Feb 25. PubMed PMID: 23437926.

2: Santos Cerqueira G, dos Santos e Silva G, Rios Vasconcelos E, Fragoso de Freitas AP, Arcanjo Moura B, Silveira Macedo D, Lopes Souto A, Barbosa Filho JM, de Almeida Leal LK, de Castro Brito GA, Souccar C, de Barros Viana GS. Effects of hecogenin and its possible mechanism of action on experimental models of gastric ulcer in mice. Eur J Pharmacol. 2012 May 15;683(1-3):260-9. doi: 10.1016/j.ejphar.2012.02.043. Epub 2012 Mar 8. PubMed PMID: 22426163.

3: Cruz MS, Cabral Barroso S, Navoni JA, Rocha Silva Teles MM, Barbosa-Filho JM, de Oliveira Rocha HA, Souza do Amaral V. Effect of Hecogenin on DNA instability. Toxicol Rep. 2016 Jun 16;3:539-543. doi: 10.1016/j.toxrep.2016.06.004. eCollection 2016. PubMed PMID: 28959577; PubMed Central PMCID: PMC5615936.

4: Poza JJ, Rodríguez J, Jiménez C. Synthesis of a new cytotoxic cephalostatin/ritterazine analogue from hecogenin and 22-epi-hippuristanol. Bioorg Med Chem. 2010 Jan 1;18(1):58-63. doi: 10.1016/j.bmc.2009.11.018. Epub 2009 Nov 12. PubMed PMID: 19948408.

5: Fernández-Herrera MA, López-Muñoz H, Hernández-Vázquez JM, López-Dávila M, Escobar-Sánchez ML, Sánchez-Sánchez L, Pinto BM, Sandoval-Ramírez J. Synthesis of 26-hydroxy-22-oxocholestanic frameworks from diosgenin and hecogenin and their in vitro antiproliferative and apoptotic activity on human cervical cancer CaSki cells. Bioorg Med Chem. 2010 Apr 1;18(7):2474-84. doi: 10.1016/j.bmc.2010.02.051. Epub 2010 Mar 1. PubMed PMID: 20303770.

6: Cheun Y, Kou Y, Stevenson B, Kim HK, Koag MC, Lee S. Synthesis of C17-OH-north unit of ritterazine G via "Red-Ox" modifications of hecogenin acetate. Steroids. 2013 Jul;78(7):639-43. doi: 10.1016/j.steroids.2013.02.015. Epub 2013 Mar 15. PubMed PMID: 23500411.

7: Liagre B, Vergne-Salle P, Leger DY, Beneytout JL. Inhibition of human rheumatoid arthritis synovial cell survival by hecogenin and tigogenin is associated with increased apoptosis, p38 mitogen-activated protein kinase activity and upregulation of cyclooxygenase-2. Int J Mol Med. 2007 Oct;20(4):451-60. PubMed PMID: 17786275.

8: Edavana VK, Dhakal IB, Williams S, Penney R, Boysen G, Yao-Borengasser A, Kadlubar S. Potential role of UGT1A4 promoter SNPs in anastrozole pharmacogenomics. Drug Metab Dispos. 2013 Apr;41(4):870-7. doi: 10.1124/dmd.112.048157. Epub 2013 Jan 31. PubMed PMID: 23371966; PubMed Central PMCID: PMC3608453.

9: Uchaipichat V, Mackenzie PI, Elliot DJ, Miners JO. Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human udp-glucuronosyltransferases. Drug Metab Dispos. 2006 Mar;34(3):449-56. Epub 2005 Dec 28. PubMed PMID: 16381668.

10: Jin JM, Liu XK, Yang CR. Three new hecogenin glycosides from fermented leaves of Agave americana. J Asian Nat Prod Res. 2003 Jun;5(2):95-103. PubMed PMID: 12765193.

11: Pettit GR, Moser BR, Herald DL, Knight JC, Chapuis JC, Zheng X. The Cephalostatins. 23. Conversion of Hecogenin to a Steroidal 1,6-Dioxaspiro[5.5]nonane Analogue for Cephalostatin 11. J Nat Prod. 2015 May 22;78(5):1067-72. doi: 10.1021/np501033u. Epub 2015 Apr 27. PubMed PMID: 25915559.

12: Li W, Fuchs PL. Polyphosphoric acid trimethylsilyl ester promoted intramolecular acylation of an olefin by a carboxylic acid: convenient construction of C-18-functionalized delta14-hecogenin acetate. Org Lett. 2003 Oct 30;5(22):4061-4. PubMed PMID: 14572249.

13: Gómez-Calvario V, Arenas-González A, Meza-Reyes S, Montiel-Smith S, Vega-Báez JL, Sandoval-Ramírez J, Hernández-Linares MG. Synthetic pathway to 22,23-dioxocholestanic chain derivatives and their usefulness for obtaining brassinosteroid analogues. Steroids. 2013 Sep;78(9):902-8. doi: 10.1016/j.steroids.2013.04.014. Epub 2013 May 3. PubMed PMID: 23643845.

14: Ingawale DK, Patel SS. Anti-Inflammatory Potential of Hecogenin in Experimental Animals: Possible Involvement of Inflammatory Cytokines and Myeloperoxidase. Drug Res (Stuttg). 2016 Dec;66(12):644-656. Epub 2016 Sep 29. PubMed PMID: 27684191.

15: Corbiere C, Liagre B, Bianchi A, Bordji K, Dauça M, Netter P, Beneytout JL. Different contribution of apoptosis to the antiproliferative effects of diosgenin and other plant steroids, hecogenin and tigogenin, on human 1547 osteosarcoma cells. Int J Oncol. 2003 Apr;22(4):899-905. PubMed PMID: 12632085.

16: Camoutsis C, Trafalis D, Pairas G, Papageorgiou A. On the formation of 4-[N,N-bis(2-chloroethyl)amino]phenyl acetic acid esters of hecogenin and aza-homo-hecogenin and their antileukemic activity. Farmaco. 2005 Oct;60(10):826-9. Epub 2005 Aug 31. PubMed PMID: 16139280.

17: Gasparotto J, Somensi N, Kunzler A, Girardi CS, de Bittencourt Pasquali MA, Ramos VM, Simoes-Pires A, Quintans-Junior LJ, Branco A, Moreira JC, Gelain DP. Hecogenin acetate inhibits reactive oxygen species production and induces cell cycle arrest and senescence in the A549 human lung cancer cell line. Anticancer Agents Med Chem. 2014;14(8):1128-35. PubMed PMID: 25115457.

18: Lee S, Jamieson D, Fuchs PL. Synthesis of C14,15-dihydro-C22,25-epi north unit of cephalostatin 1 via "red-ox" modifications of hecogenin acetate. Org Lett. 2009 Jan 1;11(1):5-8. doi: 10.1021/ol802122p. PubMed PMID: 19055428; PubMed Central PMCID: PMC2859694.

19: CHAKRAVARTI RN, MITRA MN, CHAKRAVARTI D. Hecogenin as a bye-product of the Indian sisal fibre industry. Bull Calcutta Sch Trop Med. 1962 Jan;10:3-4. PubMed PMID: 14019880.

20: Xu LX, Zhou TH. [Colorimetric method for the determination of hecogenin in Agave americana L. residue]. Yao Xue Xue Bao. 1982 Aug;17(8):609-14. Chinese. PubMed PMID: 7180493.

Hecogenin

100.0mg / USD 182.0