Showing chemical card for cis-4-Hydroxycyclohexylacetic acid (CFc000000345)
Record Information
Version
1.0
Creation Date
2022-08-28 10:25:12 UTC
Update Date
2022-09-13 18:44:42 UTC
Chemfont ID
CFc000000345
Molecule Identification
Common Name
cis-4-Hydroxycyclohexylacetic acid
Definition
cis-4-Hydroxycyclohexylacetic acid is a tyrosine metabolite that has been found in the urine of a patient with a defect of 4-hydroxyphenylpyruvate dioxygenase (or HPPD) (EC 1.13.11.27), an inborn error of metabolism (PMIDs 701419, 719903) also called hawkinsinuria. 4-Hydroxyphenylpyruvate dioxygenase participates in the tyrosine catabolic pathway by catalyzing the conversion of 4-hydroxyphenylpyruvate to homogentisate (Hager et al., 1957). The mechanism of action of 4-hydroxyphenylpyruvate dioxygenase involves a decarboxylation step and an oxidation step, followed by a rearrangement step to form homogentisic acid (Tomoeda et al., 2000). Awata et al. (1994) determined that the HPD gene contains 14 exons. Analysis of the 5-prime flanking sequence of the gene suggested that expression of the gene is regulated by hepatocyte-specific and liver-enriched transcription factors, as well as by hormones (OMIM: 609695 ). cis-4-Hydroxycyclohexylacetic acid has also been found to be a microbial metabolite (PMID: 20615997 ).
Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
Ungnade, Herbert E.; Morriss, Francis V. Hydrogenation of phenolic acids. Journal of the American Chemical Society (1948), 70 1898-9. CODEN: JACSAT ISSN:0002-7863. CAN 42:29753 AN 1948:29753
