An internal standard for the quantification of alloisolithocholic acid
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Unlabeled Version(s)
29542Alloisolithocholic Acid
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Alloisolithocholic Acid-d4

Item No. 41155

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5α)-3β-hydroxy-d4-cholan-24-oic acid
CAS Number
2410277-60-8
Synonyms
  • AILCA-d4
  • AlloisoLCA-d4
  • β-hydroxy-5-Cholenoic Acid-d4
  • IsoalloLCA-d4
  • Isoallolithocholic Acid-d4
Molecular Formula
C24H36D4O3
Formula Weight
380.6
Purity
≥99% deuterated forms (d1-d4)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble: 0.1-1 mg/ml
SMILES
C[C@H](CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C([2H])([2H])[C@@H](O)C([2H])([2H])C[C@]4(C)[C@@]3([H])CC[C@@]21C
InChi Code
InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17+,18+,19-,20+,21+,23+,24-/m1/s1/i10D2,14D2
InChi Key
SMEROWZSTRWXGI-OTNPFYSJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    5 mg

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    10 mg

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    Product Description

    Alloisolithocholic acid-d4 is intended for use as an internal standard for the quantification of alloisolithocholic acid (Item No. 29542) by GC- or LC-MS. Alloisolithocholic acid is a metabolite of the secondary bile acid metabolite 3-oxo lithocholic acid (dehydrolithocholic acid; Item No. 29544).1 It is formed from 3-oxo lithocholic acid by gut microbiota.1 Alloisolithocholic acid (20 µM) increases the association of the nuclear hormone receptor nerve growth factor IB (Nr4a1) to the gene encoding forkhead box protein P3 (Foxp3) in isolated mouse CD4+ T cells. It induces the differentiation of isolated mouse T cells into regulatory T cells (Tregs) and the production of mitochondrial reactive oxygen species (ROS) in isolated mouse CD4+ T cells when used at a concentration of 20 µM.2 Alloisolithocholic acid (6 mg/kg) reduces hepatic bile flow and bile salt, cholesterol, and phospholipid secretion, as well as induces loss of microvilli and dilation of canaliculi in hepatocytes, markers of cholestasis, in rats.3 Fecal levels of alloisolithocholic acid are reduced in patients with Crohn’s disease or ulcerative colitis.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, W., Hang, S., Fang, Y., et al. A bacterial bile acid metabolite modulates Treg activity through the nuclear hormone receptor NR4A1. Cell Host Microbe 29(9), 1366-1377.e1369 (2021).

    2. Hang, S., Paik, D., Yao, L., et al. Bile acid metabolites control TH17 and Treg cell differentiation. Nature 576(7785), 143-148 (2019).

    3. Vonk, R.J., Tuchweber, B., Massé, D., et al. Intrahepatic cholestasis induced by allo monohydroxy bile acid in rats. Gastroenterology 80(2), 242-249 (1981).