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3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (PC000957)

Record Information
Version1.0
Creation date2015-10-09 22:33:36 UTC
Update date2017-01-19 02:36:42 UTC
FoodComEx IDPC000957
FoodDB RecordFDB023037
Chemical Information
Name3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
Description(3-Hydroxyphenyl)hydracrylate (HPHPA) is an organic acid detected in human urine. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (PMID:11978597). Recently it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. Specifically HPHPA appears to arise from the action of the anaerobic bacteria Clostrida species (PMID:20423563). Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals. [HMDB]
CAS Number3247-75-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3-Hydroxyphenyl)hydracrylatehmdb
(3-Hydroxyphenyl)hydracrylic acidhmdb
3-(3-hydroxyphenyl)-3-hydroxypropanoatehmdb
3-(3-hydroxyphenyl)-3-hydroxypropanoic acidhmdb
3-(3-Hydroxyphenyl)-3-hydroxypropionatehmdb
3-(3-Hydroxyphenyl)-3-hydroxypropionic acidhmdb
3-(3-Hydroxyphenyl)hydracrylatehmdb
3-(3-Hydroxyphenyl)hydracrylic acidhmdb
3-(m-Hydroxyphenyl)hydracrylatehmdb
3-(m-Hydroxyphenyl)hydracrylic acidhmdb
3-Hydroxy-3-(3-hydroxyphenyl)propionic acidHMDB
3-Hydroxyphenyl-hydracrylic acidHMDB
3'-Hydroxyphenylhydracrylic acidHMDB
b-(m-Hydroxyphenyl)hydracrylatehmdb
b-(m-Hydroxyphenyl)hydracrylic acidhmdb
beta-(m-Hydroxyphenyl)hydracrylatehmdb
beta-(m-Hydroxyphenyl)hydracrylic acidhmdb
HPHPAhmdb
Chemical FormulaC9H10O4
IUPAC name3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
InChI IdentifierInChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
InChI KeyKHTAGVZHYUZYMF-UHFFFAOYSA-N
Isomeric SMILESOC(CC(O)=O)C1=CC(O)=CC=C1
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Phenol
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 100 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals H949280