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700070P

Avanti

trihydroxycholestanoic acid

Avanti Polar Lipids

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Synonym(s):
3α,7α,12α-trihydroxycholestanoic acid
Empirical Formula (Hill Notation):
C27H46O5
CAS Number:
547-98-8
Molecular Weight:
450.65
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700070P-1mg)

manufacturer/tradename

Avanti Polar Lipids

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

InChI key

CNWPIIOQKZNXBB-VCVMUKOKSA-N

General description

Trihydroxycholestanoic acid (THCA) is an oxidative metabolite of cholesterol and a precursor to bile acids. Very long-chain acyl-CoA synthetase (VLCS) associated with endoplasmic reticulum and peroxisomes activates THCA, the C27 bile acid intermediate.

Application

Trihydroxycholestanoic acid has been used as a sterol to test its reactivity with human mincle protein.

Biochem/physiol Actions

Trihydroxycholestanoic acid (THCA) and dihydroxycholestanoic (DHCA) accumulation is observed in Zellweger syndrome and cholestatic liver disease. The synthesis of (25R)-isomer of DHCA and THCA is favored by mitochondrial 27-hydroxylase.

Packaging

5 mL Amber Glass Screw Cap Vial (700070P-1mg)

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S Ferdinandusse et al.
Journal of lipid research, 42(1), 137-141 (2001-02-13)
We identified a new peroxisomal disorder caused by a deficiency of the enzyme alpha-methylacyl-coenzyme A (CoA) racemase. Patients with this disorder show elevated plasma levels of pristanic acid and the bile acid intermediates di- and trihydroxycholestanoic acid (DHCA and THCA)
James O'Byrne et al.
The Journal of biological chemistry, 278(36), 34237-34244 (2003-06-18)
Bile acid-CoA:amino acid N-acyltransferase (BACAT) catalyzes the conjugation of bile acids to glycine and taurine for excretion into bile. By use of site-directed mutagenesis and sequence comparisons, we have identified Cys-235, Asp-328, and His-362 as constituting a catalytic triad in
Ryoko Kiyotake et al.
The Journal of biological chemistry, 290(42), 25322-25332 (2015-08-25)
C-type lectin receptors (CLRs) are an emerging family of pattern recognition receptors that recognizes pathogens or damaged tissue to trigger innate immune responses. However, endogenous ligands for CLRs are not fully understood. In this study, we sought to identify an

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