Identification

PhytoHub ID
PHUB001584
Name
4-Hydroxymandelic acid
Systematic Name
2-hydroxy-2-(4'-hydroxyphenyl)acetic acid
Synonyms
  • (4-hydroxyphenyl)-2-hydroxyacetic acid
  • (4-hydroxyphenyl)-2-hydroxyethanoic acid
  • (4'-hydroxyphenyl)-2-hydroxyacetic acid
  • 2-Hydroxy-2-(4-hydroxyphenyl)acetic acid
  • 2-hydroxy-2-(4'-hydroxyphenyl)acetic acid
  • 2-hydroxy-2-(4’-hydroxyphenyl)ethanoic acid
  • 4-Hydroxy-L-mandelic acid
  • 4'-Hydroxymandelic acid
CAS Number
1198-84-1
Average Mass
168.148
Monoisotopic Mass
168.042258738
Chemical Formula
C8H8O4
IUPAC Name
4-hydroxymandelic acid
InChI Key
YHXHKYRQLYQUIH-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
SMILES
OC(C(O)=O)C1=CC=C(O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
7.69e+00 g/l
LogS (ALOGPS)
-1.34
LogP (ALOGPS)
0.86
Hydrogen Acceptors
4
Hydrogen Donors
3
Rotatable Bond Count
2
Polar Surface Area
77.76
Refractivity
40.68469999999999
Polarizability
15.62137864124072
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-4.105652938089659
pKa (strongest acidic)
3.3028147671822805
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Phenylacetic acids

Taxonomy of its Precursor(s)

PrecursorFamilyClassSub-class
Caffeic acid(Poly)phenol metabolitesPhenolic acid metabolitesCinnamic acidsShow Precursor
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Precursor

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Phenols
Super-class
Benzenoids
Sub-class
1-hydroxy-2-unsubstituted benzenoids
Direct Parent Name
1-hydroxy-2-unsubstituted benzenoids
Alternative Parent Names
["Alpha hydroxy acids and derivatives", "Aromatic alcohols", "Benzene and substituted derivatives", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Secondary alcohols"]
External Descriptor Annotations
["2-hydroxy carboxylic acid", "phenols"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "Alcohol", "Alpha-hydroxy acid", "Aromatic alcohol", "Aromatic homomonocyclic compound", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Hydroxy acid", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Secondary alcohol"]

Spectra

No spectra information available

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caffeic acid 4-Hydroxymandelic acidhumanNot Availablehost metabolismNot AvailableNot AvailableC8H8O4168.042258738 Publications
Orange flavanones 4-Hydroxymandelic acidhumanplasma, urinegut microbiota metaboliteNot AvailableNot Available<1%C8H8O4168.042258738 Detailed Intervention Studies

Inter-Individual Variations Metabolism

No inter-individual variations available

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