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MedKoo Cat#: 462642 | Name: Allocholic Acid
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Description:

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

Allocholic acid is a bile acid and an isomer of cholic acid. It is typically produced in the fetal or larval stages of development but has been found in adult mammals in the context of cancer or during liver regeneration in rats.

Chemical Structure

Allocholic Acid
CAS#2464-18-8

Theoretical Analysis

MedKoo Cat#: 462642

Name: Allocholic Acid

CAS#: 2464-18-8

Chemical Formula: C24H40O5

Exact Mass: 408.2876

Molecular Weight: 408.58

Elemental Analysis: C, 70.55; H, 9.87; O, 19.58

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 2 Weeks
10mg USD 400.00 2 Weeks
50mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
ACA; AlloCA; allo-Cholic; 5α-Allocholic Acid;
IUPAC/Chemical Name
(R)-4-((3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
InChi Key
BHQCQFFYRZLCQQ-PGHAKIONSA-N
InChi Code
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
SMILES Code
OC(CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@@]21C)=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 408.58 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: Bokkenheuser V, Hoshita T, Mosbach EH. Bacterial 7-dehydroxylation of cholic acid and allocholic acid. J Lipid Res. 1969 Jul;10(4):421-6. PMID: 5797529. 2: Yamasaki K, Ayaki Y, Yamasaki G. Allocholic acid, a metabolite of 7 -hydroxycholesterol in the rat and rabbit. J Biochem. 1972 May;71(5):927-9. doi: 10.1093/oxfordjournals.jbchem.a129848. PMID: 5073332. 3: Ali SS, Farhat H, Elliott WH. Bile acids. XLIX. Allocholic acid, the major bile acid of Uromastix hardwickii. J Lipid Res. 1976 Jan;17(1):21-4. PMID: 1255017. 4: Mui MM, Elliott WH. Bile acids. XXXII. Allocholic acid, a metabolite of allochenodeoxycholic acid in bile fistula rats. J Biol Chem. 1971 Jan 25;246(2):302-4. PMID: 5542000. 5: Yamasaki K, Ikawa S, Ayaki Y, Yamamoto Y. Natural occurrence of allocholic acid in ox and carp bile. J Biochem. 1972 Sep;72(3):769-72. doi: 10.1093/oxfordjournals.jbchem.a129957. PMID: 4673765. 6: KARAVOLAS HJ, ELLIOTT WH, HSIA SL, DOISY EA Jr, MATSCHINER JT, THAYER SA, DOISY EA. BILE ACIDS. XXII. ALLOCHOLIC ACID, A METABOLITE OF 5-ALPHA- CHOLESTAN-3-BET-A-OL IN THE RAT. J Biol Chem. 1965 Apr;240:1568-72. PMID: 14285492. 7: Björkhem I, Gustafsson J. On the conversion of cholestanol into allocholic acid in rat liver. Eur J Biochem. 1971 Jan;18(2):207-13. doi: 10.1111/j.1432-1033.1971.tb01232.x. PMID: 5541504. 8: Yun SS, Scott AP, Li W. Pheromones of the male sea lamprey, Petromyzon marinus L.: structural studies on a new compound, 3-keto allocholic acid, and 3-keto petromyzonol sulfate. Steroids. 2003 Mar;68(3):297-304. doi: 10.1016/s0039-128x(02)00178-2. PMID: 12628693. 9: Briggs T, Bussjaeger C. Allocholic acid, the major component in bile from the river carpsucker, Carpiodes carpio (Rafinesque) (Catostomidae). Comp Biochem Physiol B. 1972 Jul 15;42(3):493-6. doi: 10.1016/0305-0491(72)90264-7. PMID: 4644219. 10: ANDERSON IG, HASLEWOOD GA. Comparative studiesof 'bile salts'. 15. The natural occurrence and preparation of allocholic acid. Biochem J. 1962 Oct;85(1):236-42. doi: 10.1042/bj0850236. PMID: 14012853; PMCID: PMC1243935. 11: Mitra MN, Elliott WH. Bile acids. 23. A new direct synthesis of allocholic acid and its 3 beta isomer. J Org Chem. 1968 Jan;33(1):175-81. doi: 10.1021/jo01265a033. PMID: 5634890. 12: Kihira K, Shimazu K, Kuwabara M, Yoshii M, Takeuchi H, Nakano I, Ozawa S, Onuki M, Hatta Y, Hoshita T. Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. Steroids. 1986 Jul- Aug;48(1-2):109-19. doi: 10.1016/0039-128x(86)90045-0. PMID: 3660436. 13: Salen G, Tint GS, Eliav B, Deering N, Mosbach EH. Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21. doi: 10.1172/JCI107596. PMID: 11344576; PMCID: PMC301505. 14: Ridlon JM, Kang DJ, Hylemon PB. Isolation and characterization of a bile acid inducible 7alpha-dehydroxylating operon in Clostridium hylemonae TN271. Anaerobe. 2010 Apr;16(2):137-46. doi: 10.1016/j.anaerobe.2009.05.004. Epub 2009 May 21. PMID: 19464381; PMCID: PMC6262846. 15: Clayton PT, Muller DP, Lawson AM. The bile acid composition of gastric contents from neonates with high intestinal obstruction. Biochem J. 1982 Sep 15;206(3):489-98. doi: 10.1042/bj2060489. PMID: 7150258; PMCID: PMC1158615. 16: Lee SP, Tasman-Jones C, Carlisle VF. Oleic acid-induced cholelithiasis in the rabbit: conversion of dietary oleic acid to cholestanol as a cause of calcium-bile salt gallstones. Hepatology. 1987 May-Jun;7(3):529-34. doi: 10.1002/hep.1840070319. PMID: 3570164. 17: Li K, Wang H, Brant CO, Ahn S, Li W. Multiplex quantification of lamprey specific bile acid derivatives in environmental water using UHPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Dec 15;879(32):3879-86. doi: 10.1016/j.jchromb.2011.10.039. Epub 2011 Nov 4. PMID: 22104518. 18: Siefkes MJ, Li W. Electrophysiological evidence for detection and discrimination of pheromonal bile acids by the olfactory epithelium of female sea lampreys ( Petromyzon marinus). J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2004 Mar;190(3):193-9. doi: 10.1007/s00359-003-0484-1. Epub 2003 Dec 20. PMID: 14689221. 19: Haslewood GA. Bile salts of germ-free domestic fowl and pigs. Biochem J. 1971 Jun;123(1):15-8. doi: 10.1042/bj1230015. PMID: 5128663; PMCID: PMC1176895. 20: Yoshii M, Une M, Kihira K, Kuramoto T, Akizawa T, Yoshioka M, Butler VP Jr, Hoshita T. Bile salts of the toad, Bufo marinus: characterization of a new unsaturated higher bile acid, 3 alpha,7 alpha,12 alpha,26-tetrahydroxy-5 beta- cholest-23-en-27-oic acid. J Lipid Res. 1994 Sep;35(9):1646-51. PMID: 7806978.