Allocholic acid
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| Category | Others |
| Catalog number | BBF-04061 |
| CAS | 2464-18-8 |
| Molecular Weight | 408.57 |
| Molecular Formula | C24H40O5 |
| Purity | >99% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04061 | 10 mg | $199 | In stock |
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Add to cartDescription
Allocholic acid is a bile acid metabolized from animals. Allocholic acid is also a precursor to petromyzonol.
Specification
| Synonyms | 3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholan-24-oic acid; 5alpha-cholic acid; 5α-cholanic acid-3α,7α,12α-triol |
| Shelf Life | 1 Year |
| Storage | Store at -20°C |
| IUPAC Name | (4R)-4-[(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid |
| Canonical SMILES | CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C |
| InChI | 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 |
| InChI Key | BHQCQFFYRZLCQQ-PGHAKIONSA-N |
Properties
| Appearance | White Solid |
| Boiling Point | 583.9°C at 760 mmHg |
| Melting Point | 238-240°C |
| Density | 1.184 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis
M Kuwabara,S Ozawa,K Shimazu,K Kihira,Y Hatta,I Nakano,M Onuki,M Yoshii,T Hoshita,H Takeuchi Steroids . 1986 Jul-Aug;48(1-2):109-19. doi: 10.1016/0039-128x(86)90045-0.
Bile acid profiles of bile, urine, and feces obtained from a patient with cerebrotendinous xanthomatosis on the same day have been analyzed by gas-liquid chromatography-mass spectrometry after fractionation into groups by mode of conjugation by an ion-exchange chromatography. The predominant biliary bile acid was cholic acid conjugated with glycine and taurine. Lesser amounts of the amino acid conjugates of chenodeoxycholic acid, ursodeoxycholic acid, 7-ketodeoxycholic acid, allocholic acid, and deoxycholic acid, and of unconjugated norcholic acid and allonorcholic acid were also present in the bile. The major fecal bile acid was 7-epicholic acid. Relatively large amounts of bile acids were excreted in the urine. Unconjugated 7-epicholic acid, norcholic acid, allonorcholic acid, and cholic acid predominated. The bile acid profiles of the patient were different from those of normal subjects and should be useful for the diagnosis.
2. Bile acid production is life-stage and sex-dependent and affected by primer pheromones in the sea lamprey
Anne M Scott,Ugo Bussy,Skye D Fissette,Yu-Wen Chung-Davidson,Weiming Li J Exp Biol . 2021 Mar 23;224(9):jeb229476. doi: 10.1242/jeb.229476.
Pheromonal bile salts are important for sea lampreys (Petromyzon marinusLinnaeus) to complete their life cycle. The synthesis and release of a releaser/primer pheromone 3-keto petromyzonol sulfate (3kPZS) by spermiating males have been well characterized. 3kPZS evokes sexual behaviors in ovulatory females, induces immediate 3kPZS release in spermiating males, and elicits neuroendocrine responses in prespawning adults. Another primer pheromone released by spermiating males, 3-keto allocholic acid (3kACA), antagonizes the neuroendocrine effects of 3kPZS in prespermiating males. However, the effects of 3kACA and 3kPZS on pheromone production in prespawning adults is unclear. To understand the foundation of pheromone production, we examined sea lamprey bile salt levels at different life stages. To investigate the priming effects of 3kACA and 3kPZS, we exposed prespawning adults with vehicle or synthetic 3kACA or 3kPZS. We hypothesized that endogenous bile salt levels were life-stage and sex-dependent, and differentially affected by 3kACA and 3kPZS in prespawning adults. Using ultra-performance liquid chromatography tandem mass spectrometry, we found that sea lampreys contained distinct mixtures of bile salts in the liver and plasma at different life stages. Males usually contained higher amounts of bile salts than females. Petromyzonamine disulfate was the most abundant C27bile salt and petromyzonol sulfate was the most abundant C24bile salt. Waterborne 3kACA and 3kPZS exerted differential effects on bile salt production in the liver and gill, their circulation and clearance in the plasma, and their release into water. We conclude that bile salt levels are life-stage and sex-dependent and differentially affected by primer pheromones.
3. Bacterial 7-dehydroxylation of cholic acid and allocholic acid
T Hoshita,V Bokkenheuser,E H Mosbach J Lipid Res . 1969 Jul;10(4):421-6.
An obligate anaerobic organism capable of dehydroxylating cholic acid to deoxycholic acid and allocholic acid to allodeoxycholic acid was isolated from feces of the rabbit. It was a member of the bacteroides group (Gram-variable, nonsporulating anaerobes). The growth of the organism was inhibited by neomycin, 10-20 micro g/ml. The existence of this organism affords a satisfactory explanation for the development of gallstones in the cholestanol-fed rabbit and for their absence in rabbits simultaneously treated with neomycin.
4. Bile acids. XLIX. Allocholic acid, the major bile acid of Uromastix hardwickii
S S Ali,H Farhat,W H Elliott J Lipid Res . 1976 Jan;17(1):21-4.
Tauroallocholate is the major bile salt of the lizard, Uromastix hardwickii. Alkaline hydrolysis of bile from 25 gallbladders provided 1.21 g of acidic material, about 90% of which was allocholic acid. Analyses by gas-liquid chromatography, and mass spectrometry verified the presence of almost 10% of deoxycholic acid and smaller amounts of other 5alpha and 5beta-bile acids.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
