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MedKoo Cat#: 573595 | Name: Hecogenin acetate
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Description:

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

Hecogenin acetate is a steroid sapogenin that has anthelmintic and antinociceptive properties. Hecogenin acetate inhibits development of mechanical hyperalgesia induced by carrageenan, TNF-α, dopamine , and prostaglandin E2 in mice.

Chemical Structure

Hecogenin acetate
Hecogenin acetate
CAS#915-35-5

Theoretical Analysis

MedKoo Cat#: 573595

Name: Hecogenin acetate

CAS#: 915-35-5

Chemical Formula: C29H44O5

Exact Mass: 472.3189

Molecular Weight: 472.67

Elemental Analysis: C, 73.69; H, 9.38; O, 16.92

Price and Availability

Size Price Availability Quantity
1g USD 265.00 2 Weeks
5g USD 585.00 2 Weeks
10g USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Hecogenin acetate; NSC 15489; NSC15489; NSC-15489
IUPAC/Chemical Name
(2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-8-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl acetate
InChi Key
CVKZWRTYHCDWTE-RSEFXUKDSA-N
InChi Code
InChI=1S/C29H44O5/c1-16-8-11-29(32-15-16)17(2)26-24(34-29)13-23-21-7-6-19-12-20(33-18(3)30)9-10-27(19,4)22(21)14-25(31)28(23,26)5/h16-17,19-24,26H,6-15H2,1-5H3/t16-,17+,19+,20+,21-,22+,23+,24+,26+,27+,28-,29-/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](OC(C)=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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 472.67 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: Araújo NJS, Do Socorro Costa M, Da Silva ARP, Paulo CLR, Silva CAP, Felix FJ, Filho JMB, Coutinho HDM, Andrade-Pinheiro JC. Modifying-antibiotic action of Hecogenin Acetate as an alternative to combat bacterial infections. J Steroid Biochem Mol Biol. 2025 Jun;250:106721. doi: 10.1016/j.jsbmb.2025.106721. Epub 2025 Mar 17. PMID: 40107429. 2: Alamoudi AJ, Nazeer M, Shah N, Ullah S, Alshamrani M, Rizg WY, Ashour OM, Abdel-Naim AB, Shah AJ. Diuretic effects of Hecogenin and Hecogenin acetate via aldosterone synthase inhibition. Saudi Pharm J. 2024 Jul;32(7):102105. doi: 10.1016/j.jsps.2024.102105. Epub 2024 May 16. PMID: 38873334; PMCID: PMC11170188. 3: Araújo NJS, Costa MDS, da Silva ARP, Paulo CLR, Silva CAP, Felix FJ, Oliveira-Tintino CDM, Filho JMB, de Freitas TS, Braga MFBM, Coutinho HDM, Andrade-Pinheiro JC. In vitro evaluation of the susceptibility of bacterial biofilms to hecogenin acetate. Acta Trop. 2024 May;253:107157. doi: 10.1016/j.actatropica.2024.107157. Epub 2024 Feb 22. PMID: 38387772. 4: Sousa AJC, de Sousa Neto BP, da Costa DS, de Sousa MC, de Carvalho CES, Quintans-Junior LJ, Quintans JSS, Neves JA, da Silva FV, Viana AFSC, Nunes PHM, de Cássia Meneses Oliveira R. Antiulcerogenic and healing activity of hecogenin acetate in rodents. Naunyn Schmiedebergs Arch Pharmacol. 2023 Apr;396(4):759-769. doi: 10.1007/s00210-022-02341-0. Epub 2022 Dec 7. PMID: 36474020. 5: Santos Araújo NJ, Pereira da Silva AR, Costa MDS, Pereira Silva CA, Sampaio de Freitas T, Oliveira de Sousa E, Barbosa Filho JM, Lobo Soares de Matos YM, Melo Coutinho HD, Andrade-Pinheiro JC. Evaluation of the antibacterial activity of hecogenin acetate and its inhibitory potential of NorA and MepA efflux pumps from Staphylococcus aureus. Microb Pathog. 2023 Jan;174:105925. doi: 10.1016/j.micpath.2022.105925. Epub 2022 Nov 30. PMID: 36462578. 6: Zhu LC, Yang DL, Shi Y. Synthesis of 5α,6-Dihydroveragranines A and B. Org Lett. 2022 Aug 12;24(31):5825-5828. doi: 10.1021/acs.orglett.2c02367. Epub 2022 Aug 3. PMID: 35920688. 7: Santos Passos FR, Pereira EWM, Heimfarth L, Monteiro BS, Barbosa Gomes de Carvalho YM, Siqueira-Lima PS, Melo Coutinho HD, Antunes de Souza Araújo A, Guedes da Silva Almeida JR, Barreto RSS, Picot L, Quintans-Júnior LJ, Quintans JSS. Role of peripheral and central sensitization in the anti-hyperalgesic effect of hecogenin acetate, an acetylated sapogenin, complexed with β-cyclodextrin: Involvement of NFκB and p38 MAPK pathways. Neuropharmacology. 2021 Mar 15;186:108395. doi: 10.1016/j.neuropharm.2020.108395. Epub 2021 Jan 28. PMID: 33516738. 8: Santos ACV, Santos FO, Lima HG, Silva GDD, Uzêda RS, Dias ÊR, Branco A, Cardoso KV, David JM, Botura MB, Costa SL, Batatinha MJM. In vitro ovicidal and larvicidal activities of some saponins and flavonoids against parasitic nematodes of goats. Parasitology. 2018 Dec;145(14):1884-1889. doi: 10.1017/S0031182018000689. Epub 2018 May 21. PMID: 29781423. 9: de França Almeida Moreira CDL, de Oliveira Pinheiro JG, da Silva-Júnior WF, Barbosa EG, Lavra ZMM, Pereira EWM, Resende MM, de Azevedo EP, Quintans-Júnior LJ, de Souza Araújo AA, de Souza Siqueira Quintans J, de Lima ÁAN. Amorphous solid dispersions of hecogenin acetate using different polymers for enhancement of solubility and improvement of anti-hyperalgesic effect in neuropathic pain model in mice. Biomed Pharmacother. 2018 Jan;97:870-879. doi: 10.1016/j.biopha.2017.10.161. Epub 2017 Nov 7. PMID: 29136763. 10: Carvalho YMBG, Menezes PP, Sousa BMH, Lima BS, Trindade IAS, Serafini MR, Pereira EWM, Rezende MM, Quintans JSS, Quintans-Júnior LJ, Nakamura CV, Silva- Júnior EF, Crispim AC, Aquino TM, Araújo AAS. Inclusion complex between β-cyclodextrin and hecogenin acetate produces superior analgesic effect in animal models for orofacial pain. Biomed Pharmacother. 2017 Sep;93:754-762. doi: 10.1016/j.biopha.2017.06.091. Epub 2017 Jul 10. PMID: 28704800. 11: Olivero-Acosta M, Maldonado-Rojas W, Olivero-Verbel J. Natural Products as Chemopreventive Agents by Potential Inhibition of the Kinase Domain in ErbB Receptors. Molecules. 2017 Feb 17;22(2):308. doi: 10.3390/molecules22020308. PMID: 28218686; PMCID: PMC6155853. 12: Kumar RN, Lee S. Synthesis of 23-deoxy-25-epi north unit of cephalostatin 1 via reductive and oxidative modifications of hecogenin acetate. Steroids. 2017 Feb;118:68-75. doi: 10.1016/j.steroids.2016.12.012. Epub 2016 Dec 29. PMID: 28041952. 13: 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. PMID: 25915559. 14: 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. doi: 10.2174/1871520614666140408151751. PMID: 25115457. 15: Quintans JS, Barreto RS, de Lucca W Jr, Villarreal CF, Kaneto CM, Soares MB, Branco A, Almeida JR, Taranto AG, Antoniolli AR, Freitas RM, Quintans LJ Jr. Evidence for the involvement of spinal cord-inhibitory and cytokines-modulatory mechanisms in the anti-hyperalgesic effect of hecogenin acetate, a steroidal sapogenin-acetylated, in mice. Molecules. 2014 Jun 19;19(6):8303-16. doi: 10.3390/molecules19068303. PMID: 24950436; PMCID: PMC6270830. 16: Kanduluru AK, Banerjee P, Beutler JA, Fuchs PL. A convergent total synthesis of the potent cephalostatin/ritterazine hybrid -25-epi ritterostatin GN1N. J Org Chem. 2013 Sep 20;78(18):9085-92. doi: 10.1021/jo401171q. Epub 2013 Aug 29. PMID: 23899273; PMCID: PMC7511990. 17: 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. PMID: 23643845. 18: 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. PMID: 23500411. 19: 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. PMID: 23437926. 20: Kou Y, Cheun Y, Koag MC, Lee S. Synthesis of 14',15'-dehydro-ritterazine Y via reductive and oxidative functionalizations of hecogenin acetate. Steroids. 2013 Feb;78(2):304-11. doi: 10.1016/j.steroids.2012.10.021. Epub 2012 Dec 10. PMID: 23238516.