MedKoo Cat#: 528053 | Name: Dihydrobetulinic acid

Description:

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

Dihydrobetulinic acid is a bioactive chemical.

Chemical Structure

Dihydrobetulinic acid
CAS#25488-53-3

Theoretical Analysis

MedKoo Cat#: 528053

Name: Dihydrobetulinic acid

CAS#: 25488-53-3

Chemical Formula: C30H50O3

Exact Mass: 458.3760

Molecular Weight: 458.73

Elemental Analysis: C, 78.55; H, 10.99; O, 10.46

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
Dihydrobetulinic acid
IUPAC/Chemical Name
(3beta)-3-Hydroxylupan-28-oic acid
InChi Key
PZXJOHSZQAEJFE-FZFNOLFKSA-N
InChi Code
InChI=1S/C30H50O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h18-24,31H,8-17H2,1-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
SMILES Code
CC1(C)[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]4([H])[C@@]5([H])[C@H](C(C)C)CC[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[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
>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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 458.73 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: Eignerova B, Tichy M, Krasulova J, Kvasnica M, Rarova L, Christova R, Urban M, Bednarczyk-Cwynar B, Hajduch M, Sarek J. Synthesis and antiproliferative properties of new hydrophilic esters of triterpenic acids. Eur J Med Chem. 2017 Nov 10;140:403-420. doi: 10.1016/j.ejmech.2017.09.041. Epub 2017 Sep 21. PubMed PMID: 28987603. 2: Borkova L, Jasikova L, Rehulka J, Frisonsova K, Urban M, Frydrych I, Popa I, Hajduch M, Dickinson NJ, Vlk M, Dzubak P, Sarek J. Synthesis of cytotoxic 2,2-difluoroderivatives of dihydrobetulinic acid and allobetulin and study of their impact on cancer cells. Eur J Med Chem. 2015;96:482-90. doi: 10.1016/j.ejmech.2015.03.068. Epub 2015 Apr 1. PubMed PMID: 25942059. 3: Sengupta T, Mukherjee M, Das A, Mandal C, Das R, Mukherjee T, Majumder HK. Characterization of the ATPase activity of topoisomerase II from Leishmania donovani and identification of residues conferring resistance to etoposide. Biochem J. 2005 Sep 1;390(Pt 2):419-26. PubMed PMID: 15901238; PubMed Central PMCID: PMC1198921. 4: Kashiwada Y, Sekiya M, Ikeshiro Y, Fujioka T, Kilgore NR, Wild CT, Allaway GP, Lee KH. 3-O-Glutaryl-dihydrobetulin and related monoacyl derivatives as potent anti-HIV agents. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5851-3. PubMed PMID: 15501054. 5: Mukherjee R, Jaggi M, Rajendran P, Srivastava SK, Siddiqui MJ, Vardhan A, Burman AC. Synthesis of 3-O-acyl/3-benzylidene/3-hydrazone/3-hydrazine/17-carboxyacryloyl ester derivatives of betulinic acid as anti-angiogenic agents. Bioorg Med Chem Lett. 2004 Jun 21;14(12):3169-72. PubMed PMID: 15149668. 6: Chowdhury AR, Mandal S, Goswami A, Ghosh M, Mandal L, Chakraborty D, Ganguly A, Tripathi G, Mukhopadhyay S, Bandyopadhyay S, Majumder HK. Dihydrobetulinic acid induces apoptosis in Leishmania donovani by targeting DNA topoisomerase I and II: implications in antileishmanial therapy. Mol Med. 2003 Jan-Feb;9(1-2):26-36. PubMed PMID: 12765337; PubMed Central PMCID: PMC1430381. 7: Symon AV, Kaplun AP, Vlasenkova NK, Gerasimova GK, Shon le B, Litvin EF, Kozlova LM, Surkova EL, Shvets VI. [Epimerization of hydroxyl group in the lupan series of triterpenes]. Bioorg Khim. 2003 Mar-Apr;29(2):208-13. Russian. PubMed PMID: 12708322. 8: Hashimoto F, Kashiwada Y, Cosentino LM, Chen CH, Garrett PE, Lee KH. Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem. 1997 Dec;5(12):2133-43. PubMed PMID: 9459011. 9: Kashiwada Y, Hashimoto F, Cosentino LM, Chen CH, Garrett PE, Lee KH. Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J Med Chem. 1996 Mar 1;39(5):1016-7. PubMed PMID: 8676334. 10: Fujioka T, Kashiwada Y, Kilkuskie RE, Cosentino LM, Ballas LM, Jiang JB, Janzen WP, Chen IS, Lee KH. Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids. J Nat Prod. 1994 Feb;57(2):243-7. PubMed PMID: 8176401.