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Allocholic acid Sale

(Synonyms: 别胆酸) 目录号 : GC60044

Allocholic acid 是一种在脊椎动物中发现的胆汁酸,在肝脏再生和致癌过程中会重新出现。Allocholic acid 还是成熟嗅觉系统的一种有效而特定的刺激物。

Allocholic acid Chemical Structure

Cas No.:2464-18-8

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产品描述

Allocholic acid is a typically fetal bile acid found in vertebrates and reappears during liver regeneration and carcinogenesis. Allocholic acid is also a potent and specific stimulant of the adult olfactory system[1][2][3].

别胆酸是一种典型的胎儿胆汁酸,存在于脊椎动物中,并在肝再生和癌变过程中重新出现。 Allocholic acid 也是成人嗅觉系统的有效和特异性兴奋剂[1][2][3]。

[1]. ThomasBriggs, et al. 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. [2]. Li W, et al. The olfactory system of migratory adult sea lamprey (Petromyzon marinus) is specifically and acutely sensitive to unique bile acids released by conspecific larvae. J Gen Physiol. 1995 May;105(5):569-87. [3]. Mendoza ME, et al. Physiological characteristics of allo-cholic acid. J Lipid Res. 2003 Jan;44(1):84-92.

Chemical Properties

Cas No. 2464-18-8 SDF
别名 别胆酸
Canonical SMILES C[C@H](CCC(O)=O)[C@H]1CC[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@]12C
分子式 C24H40O5 分子量 408.57
溶解度 DMSO: 125 mg/mL (305.95 mM) 储存条件 Store at -20°C
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1 mM 2.4476 mL 12.2378 mL 24.4756 mL
5 mM 0.4895 mL 2.4476 mL 4.8951 mL
10 mM 0.2448 mL 1.2238 mL 2.4476 mL
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Research Update

Bacterial 7-dehydroxylation of cholic acid and Allocholic acid

J Lipid Res 1969 Jul;10(4):421-6.PMID:5797529doi

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.

Bile acids. XLIX. Allocholic acid, the major bile acid of Uromastix hardwickii

J Lipid Res 1976 Jan;17(1):21-4.PMID:1255017doi

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.

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.PMID:12628693DOI:10.1016/s0039-128x(02)00178-2.

This study reports the results of chemical and chromatographic studies which establish the presence of 3-keto Allocholic acid (3kACA) in water extracts from spermiating male sea lamprey, Petromyzon marinus. This is the second compound to be isolated and identified from these extracts. The first was 3-keto petromyzonol sulfate (3kPZS), which was shown to act as strong pheromonal attractant for ovulated females. Some new characterization data on 3kPZS (utilizing an only recently available synthetic preparation of the compound) is also included. The possibility that a mixture of 3kACA and 3kPZS might be a more potent pheromonal attractant than either compound alone is discussed.

Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis

Steroids 1986 Jul-Aug;48(1-2):109-19.PMID:3660436DOI: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.

Bile acid production is life-stage and sex-dependent and affected by primer pheromones in the sea lamprey

J Exp Biol 2021 Mar 23;224(9):jeb229476.PMID:33758020DOI:10.1242/jeb.229476.

Pheromonal bile salts are important for sea lampreys (Petromyzon marinus Linnaeus) 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 C27 bile salt and petromyzonol sulfate was the most abundant C24 bile 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.