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(S)-4-hydroxymandelic acid

PubChem CID
439940
Structure
(S)-4-hydroxymandelic acid_small.png
(S)-4-hydroxymandelic acid_3D_Structure.png
Molecular Formula
Synonyms
  • (S)-4-hydroxymandelic acid
  • 13244-75-2
  • (2S)-hydroxy(4-hydroxyphenyl)ethanoic acid
  • (2S)-2-hydroxy-2-(4-hydroxyphenyl)acetic acid
  • L-p-Hydroxymandelic acid
Molecular Weight
168.15 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-25
Description
(S)-4-hydroxymandelic acid is a 4-hydroxymandelic acid that has S-configuration. It is a (2S)-2-hydroxy monocarboxylic acid and a 4-hydroxymandelic acid. It is a conjugate acid of a (S)-4-hydroxymandelate. It is an enantiomer of a (R)-4-hydroxymandelic acid.
See also: (S)-4-Hydroxymandelate (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(S)-4-hydroxymandelic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-hydroxy-2-(4-hydroxyphenyl)acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)/t7-/m0/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

YHXHKYRQLYQUIH-ZETCQYMHSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1=CC(=CC=C1[C@@H](C(=O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H8O4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

13244-75-2

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 DrugBank ID

2.3.5 KEGG ID

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
168.15 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
168.04225873 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
168.04225873 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
77.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
160
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
GCMS-2010 Plus, Shimadzu
Instrument Type
EI-B
Ionization Mode
positive
Retention Time
726.11
Top 5 Peaks

267.200000 100

268.200000 23.49

147.150000 10.06

269.200000 9.11

341.200000 8.01

Thumbnail
Thumbnail
License
CC BY-SA

4.1.2 Other MS

Authors
Miyagawa H, Akimoto S, Yamasaki K, GL Sciences Inc.
Instrument
GCMS-2010 Plus, Shimadzu
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Column Name
InertCap 5MS/NP 0.25 mmI.D. x 30 m, df=0.25 um
Retention Time
726.11
Top 5 Peaks

267.2 999

268.2 235

147.15 100

269.2 91

341.2 80

Thumbnail
Thumbnail
License
CC BY-SA

6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 Springer Nature References

7.3 Thieme References

7.4 Chemical Co-Occurrences in Literature

7.5 Chemical-Gene Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

8.3 Chemical Co-Occurrences in Patents

8.4 Chemical-Disease Co-Occurrences in Patents

8.5 Chemical-Gene Co-Occurrences in Patents

9 Interactions and Pathways

9.1 Protein Bound 3D Structures

9.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

9.2 Chemical-Target Interactions

10 Classification

10.1 ChEBI Ontology

10.2 ChemIDplus

10.3 NORMAN Suspect List Exchange Classification

10.4 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. ChEBI
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
    (2S)-hydroxy(4-hydroxyphenyl)ethanoic acid
    https://www.drugbank.ca/drugs/DB07896
  5. Japan Chemical Substance Dictionary (Nikkaji)
  6. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  7. MassBank Europe
  8. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  9. Metabolomics Workbench
  10. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    4-hydroxymandelic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  11. Protein Data Bank in Europe (PDBe)
  12. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  13. Springer Nature
  14. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  15. Wikidata
    (2S)-hydroxy(4-hydroxyphenyl)ethanoic acid
    https://www.wikidata.org/wiki/Q27097105
  16. PubChem
  17. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  18. PATENTSCOPE (WIPO)
  19. NCBI
CONTENTS