MedKoo Cat#: 412899 | Name: Cimigenol

Description:

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

Cimigenol is an active compound isolated from Cimicifuga, with potent anti-tumor activity.

Chemical Structure

Cimigenol
Cimigenol
CAS#3779-59-7

Theoretical Analysis

MedKoo Cat#: 412899

Name: Cimigenol

CAS#: 3779-59-7

Chemical Formula: C30H48O5

Exact Mass: 488.3502

Molecular Weight: 488.71

Elemental Analysis: C, 73.73; H, 9.90; O, 16.37

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
Cimigenol; UNII-SN559V4Y83
IUPAC/Chemical Name
(3beta,15alpha,16alpha,23R,24S)-16,23:16,24-Diepoxy-9,19-cyclolanostane-3,15,25-triol
InChi Key
CNBHUROFMYCHGI-AGUQLYCLSA-N
InChi Code
InChI=1S/C30H48O5/c1-16-14-17-22(25(4,5)33)35-30(34-17)21(16)26(6)12-13-29-15-28(29)11-10-20(31)24(2,3)18(28)8-9-19(29)27(26,7)23(30)32/h16-23,31-33H,8-15H2,1-7H3/t16-,17-,18+,19+,20+,21-,22+,23-,26-,27-,28-,29?,30-/m1/s1
SMILES Code
CC1(C)[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@H](C)C[C@]6([H])[C@H]7C(C)(O)C)[C@](O7)(O6)[C@H](O)[C@](C)5[C@]4([H])CC[C@@]12[H]
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

Preparing Stock Solutions

The following data is based on the product molecular weight 488.71 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: Jöhrer K, Stuppner H, Greil R, Çiçek SS. Structure-Guided Identification of Black Cohosh (Actaea racemosa) Triterpenoids with In Vitro Activity against Multiple Myeloma. Molecules. 2020 Feb 11;25(4):766. doi: 10.3390/molecules25040766. PMID: 32053921; PMCID: PMC7070908. 2: Xia HM, Dai YP, Sun LL. [Research progress on cycloartane triterpenoids of Actaea]. Zhongguo Zhong Yao Za Zhi. 2018 Oct;43(20):4000-4010. Chinese. doi: 10.19540/j.cnki.cjcmm.20180703.011. PMID: 30486523. 3: Sakurai N, Kozuka M, Tokuda H, Mukainaka T, Enjo F, Nishino H, Nagai M, Sakurai Y, Lee KH. Cancer preventive agents. Part 1: chemopreventive potential of cimigenol, cimigenol-3,15-dione, and related compounds. Bioorg Med Chem. 2005 Feb 15;13(4):1403-8. doi: 10.1016/j.bmc.2004.10.062. PMID: 15670948. 4: Yoshimitsu H, Nishida M, Sakaguchi M, Nohara T. Two new 15-deoxycimigenol- type and three new 24-epi-cimigenol-type glycosides from Cimicifuga Rhizome. Chem Pharm Bull (Tokyo). 2006 Sep;54(9):1322-5. doi: 10.1248/cpb.54.1322. PMID: 16946545. 5: Wang Y, Sha C, Liu W, Gai Y, Zhang H, Qu H, Wang W. Simultaneous determination of cimicifugoside H-2, cimicifugoside H-1, 23-epi-26-deoxyactein, cimigenol xyloside and 25-O-acetylcimigenoside in beagle dog plasma by LC-MS/MS. J Pharm Biomed Anal. 2012 Mar 25;62:87-95. doi: 10.1016/j.jpba.2011.11.029. Epub 2011 Dec 9. PMID: 22285707. 6: Takemoto T, Kusano G. [Studies on the constituents of cimicifuga spp. IV. Constituents of Cimicifuga acerina. (4). Structure of methyl cimigenol]. Yakugaku Zasshi. 1968 May;88(5):623-6. Japanese. doi: 10.1248/yakushi1947.88.5_623. PMID: 5750285. 7: Wu HF, Li PF, Zhu YD, Zhang XP, Ma GX, Xu XD, Liu YL, Luo ZH, Chen DZ, Zou QY, Zhao ZJ. Soulieoside O, a new cyclolanostane triterpenoid glycoside from Souliea vaginata. J Asian Nat Prod Res. 2017 Dec;19(12):1177-1182. doi: 10.1080/10286020.2017.1307190. Epub 2017 Apr 4. PMID: 28374633. 8: Nian Y, Wang HY, Zhou L, Su J, Li Y, Qiu MH. Cytotoxic cycloartane triterpenes of the traditional Chinese medicine "shengma" (Cimicifuga dahurica). Planta Med. 2013 Jan;79(1):60-9. doi: 10.1055/s-0032-1328019. Epub 2012 Dec 5. PMID: 23225366. 9: Sakurai N, Kozuka M, Tokuda H, Nobukuni Y, Takayasu J, Nishino H, Kusano A, Kusano G, Nagai M, Sakurai Y, Lee KH. Antitumor agents 220. Antitumor-promoting effects of cimigenol and related compounds on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis. Bioorg Med Chem. 2003 Mar 20;11(6):1137-40. doi: 10.1016/s0968-0896(02)00432-7. PMID: 12614901. 10: Choi JY, Jeon SJ, Son KH, Park YI, Dong MS. Induction of mast cell degranulation by triterpenoidal saponins obtained from Cimicifugae rhizoma. Immunopharmacol Immunotoxicol. 2016 Oct;38(5):311-8. doi: 10.1080/08923973.2016.1201101. Epub 2016 Jul 1. PMID: 27310149.