Synonym
4-Hydroxyphenylglyoxylate, 4-Hydroxyphenylglyoxylic acid, para-Hydroxybenzoylformic acid, Pisolithin A
IUPAC/Chemical Name
2-(4-hydroxyphenyl)-2-oxoacetic acid
InChi Key
KXFJZKUFXHWWAJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H6O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,9H,(H,11,12)
SMILES Code
OC(C(c1ccc(O)cc1)=O)=O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
166.13
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Kope HH, Tsantrizos YS, Fortin JA, Ogilvie KK. p-Hydroxybenzoylformic acid and (R)-(-)-p-hydroxymandelic acid, two antifungal compounds isolated from the liquid culture of the ectomycorrhizal fungus Pisolithus arhizus. Can J Microbiol. 1991 Apr;37(4):258-64. doi: 10.1139/m91-040. PMID: 1913337.
2: Diez V, Loznik M, Taylor S, Winn M, Rattray NJ, Podmore H, Micklefield J, Goodacre R, Medema MH, Müller U, Bovenberg R, Janssen DB, Takano E. Functional Exchangeability of Oxidase and Dehydrogenase Reactions in the Biosynthesis of Hydroxyphenylglycine, a Nonribosomal Peptide Building Block. ACS Synth Biol. 2015 Jul 17;4(7):796-807. doi: 10.1021/sb500368w. Epub 2015 Mar 9. PMID: 25713978.
3: Cook GA, Mynatt RL, Kashfi K. Yonetani-Theorell analysis of hepatic carnitine palmitoyltransferase-I inhibition indicates two distinct inhibitory binding sites. J Biol Chem. 1994 Mar 25;269(12):8803-7. PMID: 8132614.
4: Higgins AJ, Morville M, Burges RA, Blackburn KJ. Mechanism of action of oxfenicine on muscle metabolism. Biochem Biophys Res Commun. 1981 May 15;100(1):291-6. doi: 10.1016/s0006-291x(81)80095-2. PMID: 7259751.
5: Stephens TW, Harris RA. Effect of starvation and diabetes on the sensitivity of carnitine palmitoyltransferase I to inhibition by 4-hydroxyphenylglyoxylate. Biochem J. 1987 Apr 15;243(2):405-12. doi: 10.1042/bj2430405. PMID: 2820379; PMCID: PMC1147869.
6: Stephens TW, Higgins AJ, Cook GA, Harris RA. Two mechanisms produce tissue- specific inhibition of fatty acid oxidation by oxfenicine. Biochem J. 1985 Apr 15;227(2):651-60. doi: 10.1042/bj2270651. PMID: 4004784; PMCID: PMC1144885.
7: Kashfi K, Cook GA. Proteinase treatment of intact hepatic mitochondria has differential effects on inhibition of carnitine palmitoyltransferase by different inhibitors. Biochem J. 1992 Mar 15;282 ( Pt 3)(Pt 3):909-14. doi: 10.1042/bj2820909. PMID: 1554374; PMCID: PMC1130873.
8: Guzmán M, Azzolin IR, Moulin CC, Perry ML. Pre- and postnatal protein undernutrition increases hepatic carnitine palmitoyltransferase I activity and decreases enzyme sensitivity to inhibitors in the suckling rat. Horm Metab Res. 1992 Oct;24(10):471-3. doi: 10.1055/s-2007-1003365. PMID: 1464412.
