MedKoo Cat#: 571056 | Name: Ceanothic acid

Description:

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

Ceanothic acid, the A-1 homologue of betulinic acid, is isolated from Ceanothus americanus. Synthesized compounds from ceanothic acid have been shown to inhibit Epstein-Barr virus early antigen activation in anti-cancer research. It also demonstrates growth inhibitory effect against Streptococcus mutans, Actinomyces viscosus, Porphyromonas gingivalis, and Prevotella.

Chemical Structure

Ceanothic acid
CAS#21302-79-4

Theoretical Analysis

MedKoo Cat#: 571056

Name: Ceanothic acid

CAS#: 21302-79-4

Chemical Formula: C30H46O5

Exact Mass: 486.3345

Molecular Weight: 486.69

Elemental Analysis: C, 74.04; H, 9.53; O, 16.44

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 #
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Synonym
Ceanothic acid
IUPAC/Chemical Name
(1R,2R,3aR,5aR,5bR,7aR,10S,10aR,10bR,12aR,12bR)-2-hydroxy-3,3,5a,5b,12b-pentamethyl-10-(prop-1-en-2-yl)octadecahydrodicyclopenta[a,i]phenanthrene-1,7a(1H)-dicarboxylic acid
InChi Key
WLCHQSHZHFLMJH-GOWUPVHISA-N
InChi Code
InChI=1S/C30H46O5/c1-16(2)17-10-13-30(25(34)35)15-14-27(5)18(21(17)30)8-9-20-28(27,6)12-11-19-26(3,4)23(31)22(24(32)33)29(19,20)7/h17-23,31H,1,8-15H2,2-7H3,(H,32,33)(H,34,35)/t17-,18-,19+,20+,21-,22-,23-,27-,28-,29+,30-/m1/s1
SMILES Code
C[C@@]1([C@]2(C)CC3)CC[C@@H](C(C)(C)[C@@H]([C@@H]4C(O)=O)O)[C@@]4(C)[C@H]1CC[C@@H]2[C@@H]5[C@@]3(C(O)=O)CC[C@@H]5C(C)=C
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 486.69 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: Lee SS, Chen WC, Huang CF, Su Y. Preparation and cytotoxic effect of ceanothic acid derivatives. J Nat Prod. 1998 Nov;61(11):1343-7. PubMed PMID: 9834149. 2: Guo S, Duan JA, Zhao JL, Qian DW, Zhang WJ. [Chemical constituents from seeds of Ziziphus mauritiana]. Zhong Yao Cai. 2014 Mar;37(3):432-5. Chinese. PubMed PMID: 25174108. 3: Su Y, Chang CL, Lee SS, Chen WC, Huang CF. In vitro cytotoxic activity of 1-decarboxy-3-oxo-ceanothic acid in a human ovarian adenocarcinoma cell line. Res Commun Mol Pathol Pharmacol. 1998 Jun;100(3):313-26. PubMed PMID: 9730010. 4: Nakagawa-Goto K, Yamada K, Taniguchi M, Tokuda H, Lee KH. Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents. Bioorg Med Chem Lett. 2009 Jul 1;19(13):3378-81. doi: 10.1016/j.bmcl.2009.05.050. Epub 2009 May 18. PubMed PMID: 19481937; PubMed Central PMCID: PMC2747314. 5: Suksamrarn S, Panseeta P, Kunchanawatta S, Distaporn T, Ruktasing S, Suksamrarn A. Ceanothane- and lupane-type triterpenes with antiplasmodial and antimycobacterial activities from Ziziphus cambodiana. Chem Pharm Bull (Tokyo). 2006 Apr;54(4):535-7. PubMed PMID: 16595959. 6: Ji CJ, Zeng GZ, Han J, He WJ, Zhang YM, Tan NH. Zizimauritic acids A-C, three novel nortriterpenes from Ziziphus mauritiana. Bioorg Med Chem Lett. 2012 Oct 15;22(20):6377-80. doi: 10.1016/j.bmcl.2012.08.074. Epub 2012 Aug 26. PubMed PMID: 22989532. 7: Guo S, Duan JA, Tang Y, Su S, Shang E, Ni S, Qian D. High-performance liquid chromatography--two wavelength detection of triterpenoid acids from the fruits of Ziziphus jujuba containing various cultivars in different regions and classification using chemometric analysis. J Pharm Biomed Anal. 2009 Jul 12;49(5):1296-302. doi: 10.1016/j.jpba.2009.03.006. Epub 2009 Mar 20. PubMed PMID: 19359121. 8: Guo S, Duan JA, Tang Y, Qian Y, Zhao J, Qian D, Su S, Shang E. Simultaneous qualitative and quantitative analysis of triterpenic acids, saponins and flavonoids in the leaves of two Ziziphus species by HPLC-PDA-MS/ELSD. J Pharm Biomed Anal. 2011 Sep 10;56(2):264-70. doi: 10.1016/j.jpba.2011.05.025. Epub 2011 May 20. PubMed PMID: 21665400. 9: Li XC, Cai L, Wu CD. Antimicrobial compounds from Ceanothus americanus against oral pathogens. Phytochemistry. 1997 Sep;46(1):97-102. PubMed PMID: 9276981.