(S)-4-hydroxymandelic acid
PubChem CID
439940
Structure
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).
Chemical Structure Depiction
(2S)-2-hydroxy-2-(4-hydroxyphenyl)acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)
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)
YHXHKYRQLYQUIH-ZETCQYMHSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)
C1=CC(=CC=C1[C@@H](C(=O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C8H8O4
Computed by PubChem 2.2 (PubChem release 2024.11.20)
13244-75-2
- (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
- S)-p-hydroxymandelic acid
- 4-hydroxy-L-mandelic acid
- (+)-p-Hydroxymandelic acid
- 4-Hydroxymandelic acid, L-
- G3FLY66R5P
- (+)-4-Hydroxymandelic acid
- 4-Hydroxymandelic acid, (S)-
- Mandelic acid, p-hydroxy-, L-
- (2S)-hydroxy(4-hydroxyphenyl)acetic acid
- L-p-hydroxymandelate
- (S)-2-Hydroxy-2-(4-hydroxyphenyl)acetic acid
- L-4-hydroxymandelate
- HHH
- UNII-G3FLY66R5P
- SCHEMBL1957930
- CHEBI:32802
- YHXHKYRQLYQUIH-ZETCQYMHSA-N
- DB07896
- PD004911
- DB-258240
- (alphaS)-alpha,4-Dihydroxybenzeneacetic acid
- (S)-2-Hydroxy-2-(4-hydroxyphenyl)aceticacid
- C03198
- F75930
- Benzeneacetic acid, alpha,4-dihydroxy-, (alphaS)
- Q27097105
- (.ALPHA.S)-.ALPHA.,4-DIHYDROXYBENZENEACETIC ACID
- BENZENEACETIC ACID, .ALPHA.,4-DIHYDROXY-, (.ALPHA.S)
Property Name
Property Value
Reference
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)
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
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
License
CC BY-SA
Accession ID
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
License
CC BY-SA
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
(S)-4-Hydroxymandelate (annotation moved to)
Protein Structures Count
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=YHXHKYRQLYQUIH-ZETCQYMHSA-N
- ChEBI(S)-4-hydroxymandelic acidhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32802
- ChemIDplus4-Hydroxymandelic acid, (S)-https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0013244752ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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#linking4-HYDROXYMANDELIC ACID, (S)-https://gsrs.ncats.nih.gov/ginas/app/beta/substances/G3FLY66R5P
- DrugBankLICENSECreative 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 acidhttps://www.drugbank.ca/drugs/DB07896
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.html
- MassBank Europe4-HydroxyMandelic acidhttps://massbank.eu/MassBank/Result.jsp?inchikey=YHXHKYRQLYQUIH-ZETCQYMHSA-N
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench(S)-4-hydroxymandelic acidhttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=52067
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/4-hydroxymandelic acidNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData 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
- Springer Nature
- Thieme ChemistryLICENSEThe 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/
- Wikidata(2S)-hydroxy(4-hydroxyphenyl)ethanoic acidhttps://www.wikidata.org/wiki/Q27097105
- PubChem
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 390068984https://pubchem.ncbi.nlm.nih.gov/substance/390068984
- NCBI
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