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2-Hydroxy-3-methylbutyric acid

PubChem CID
99823
Structure
2-Hydroxy-3-methylbutyric acid_small.png
2-Hydroxy-3-methylbutyric acid_3D_Structure.png
Molecular Formula
Synonyms
  • 2-Hydroxy-3-methylbutyric acid
  • 4026-18-0
  • 2-Hydroxy-3-methylbutanoic acid
  • 2-Hydroxyisovaleric acid
  • alpha-hydroxyisovaleric acid
Molecular Weight
118.13 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
2-hydroxy-3-methylbutyric acid is a valine derivative that is valine in which the amino group has been replaced by a hydroxy group. It has a role as a human metabolite. It is functionally related to an isovaleric acid. It is a conjugate acid of a 2-hydroxy-3-methylbutyrate.
2-Hydroxy-3-methylbutyric acid has been reported in Streptomyces cavourensis, Streptomyces bacillaris, and other organisms with data available.
2-Hydroxy-3-methylbutyric acid is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2-Hydroxy-3-methylbutyric acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxy-3-methylbutanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

NGEWQZIDQIYUNV-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(C)C(C(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C5H10O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

600-37-3

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-hydroxyisovalerate
  • 2-hydroxyisovaleric acid
  • 2-hydroxyisovaleric acid, (R)-isomer
  • 2-hydroxyisovaleric acid, (S)-isomer
  • 2-hydroxyisovaleric acid, calcium (2:1) salt
  • 2-hydroxyisovaleric acid, monosodium salt, (S)-isomer
  • alpha-hydroxyisovaleric acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
118.13 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
118.062994177 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
118.062994177 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
57.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
87.7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
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 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Solubility

350 mg/mL

3.2.3 Collision Cross Section

118.65 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

3.2.4 Kovats Retention Index

Semi-standard non-polar
1063.3

3.3 Chemical Classes

3.3.1 Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
2.00:10.43, 2.01:10.62, 1.99:8.65, 3.83:39.11, 0.95:97.78, 2.03:3.27, 0.83:98.50, 0.96:100.00, 0.81:96.48, 1.98:3.77, 3.84:38.00, 2.02:8.21, 2.02:7.91, 2.00:8.79, 1.98:3.22, 2.04:3.00
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
219835
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker WM-360
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
0.85:18.26:0.42, 3.84:79.98:1.00, 0.79:18.26:0.43, 0.96:21.27:0.78, 2.01:34.17:0.31
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 4
View All
NIST Number
154827
Library
Main library
Total Peaks
79
m/z Top Peak
76
m/z 2nd Highest
73
m/z 3rd Highest
43
Thumbnail
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2 of 4
View All
NIST Number
414671
Library
Replicate library
Total Peaks
42
m/z Top Peak
76
m/z 2nd Highest
73
m/z 3rd Highest
55
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4.3.2 MS-MS

1 of 5
View All
Spectra ID
Instrument Type
LC-ESI-IT
Ionization Mode
negative
Top 5 Peaks

71.0 100

99.1 1.20

73.0 0.20

59.2 0.20

71.9 0.20

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Notes
instrument=LTQ XL, Thermo Finnigan
2 of 5
View All
Spectra ID
Instrument Type
Linear Ion Trap
Ionization Mode
negative
Top 5 Peaks

70.940629 100

98.956142 1.03

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Notes
instrument=Thermo Finnigan LTQ

4.3.3 LC-MS

1 of 5
View All
Authors
Evans A M, Mitchell M, DeHaven C D, Barrett T, Milgram E, Metabolon Inc.
Instrument
LTQ XL, Thermo Finnigan
Instrument Type
LC-ESI-IT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
40
Precursor m/z
117.1
Precursor Adduct
[M-H]-
Top 5 Peaks

71 999

99.1 12

59.2 2

71.9 2

73 2

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License
CC BY-NC-ND
2 of 5
View All
Authors
Sawada Y, Matsuda F, and Hirai MY. Plant Science Center, RIKEN
Instrument
TQD, Waters
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10
Precursor m/z
117.1
Top 5 Peaks

117 999

116 56

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License
CC BY-NC
Reference
Sawada, Y.; Akiyama, K.; Sakata, A.; Kuwahara, A.; Otsuki, H.; Sakurai, T.; Saito, K.; Hirai, M. Y. Widely Targeted Metabolomics Based on Large-Scale MS/MS Data for Elucidating Metabolite Accumulation Patterns in Plants. Plant and Cell Physiology 2008, 50 (1), 37-47. DOI:10.1093/pcp/pcn183

4.4 IR Spectra

4.4.1 FTIR Spectra

Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
219835
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
219835
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Catalog Number
219835
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Human Metabolite Information

9.1.1 Tissue Locations

Placenta

9.1.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Membrane

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (97.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

STOT SE 3 (97.4%)

11 Associated Disorders and Diseases

Disease
Pregnancy
References

PubMed: 3252730, 663967, 12833386, 2994907, 17704099, 12698507, 17061063, 16925883, 22420377, 18059417, 22494326, 23159745, 23313728, 23535240, 24704061

The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.

Disease
Maple syrup urine disease
References

PubMed: 12101068, 10508118, 10472531, 19551947, 11978597, 10234605, 6422161, 23430924, 18088602

MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Peritoneal dialysis in maple-syrup-urine disease: Studies on branched-chain amino and keto acids. Eur J Pediatr (1980) 134: 57. https://doi.org/10.1007/BF00442404

Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart
Disease
Dihydrolipoamide Dehydrogenase Deficiency
References

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Chemical Co-Occurrences in Literature

12.5 Chemical-Gene Co-Occurrences in Literature

12.6 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 LIPID MAPS Classification

16.4 ChemIDplus

16.5 ChEMBL Target Tree

16.6 UN GHS Classification

16.7 NORMAN Suspect List Exchange Classification

16.8 CCSBase Classification

16.9 EPA DSSTox Classification

16.10 The Natural Products Atlas Classification

16.11 LOTUS Tree

16.12 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. 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
  7. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    2-Hydroxy-3-methylbutyric acid
    http://www.hmdb.ca/metabolites/HMDB0000407
  8. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  9. ChEBI
  10. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    2-Hydroxy-3-methylbutyric acid
    https://www.wikidata.org/wiki/Q27104874
  11. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
    2-Hydroxy-3-methylbutyric acid
    https://www.ymdb.ca/compounds/YMDB01318
  12. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  13. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
    2-Hydroxy-3-methylbutyric acid
    https://foodb.ca/compounds/FDB022023
  14. SpectraBase
    2-Hydroxy-3-methylbutyric acid
    https://spectrabase.com/spectrum/FDC6InDIvGK
    2-HYDROXY-3-METHYLBUTYRIC ACID
    https://spectrabase.com/spectrum/DuT8YEZp7xr
    2-Hydroxy-3-methyl-butanoic acid
    https://spectrabase.com/spectrum/KOGt7y8oHJy
    2-Hydroxy-3-methylbutyric acid
    https://spectrabase.com/spectrum/FJRZ20tQfwD
    2-Hydroxy-3-methylbutyric acid
    https://spectrabase.com/spectrum/6OaDV6QJ0Lw
    2-Hydroxy-3-methylbutyric acid
    https://spectrabase.com/spectrum/3PeMDvf9N6M
  15. Japan Chemical Substance Dictionary (Nikkaji)
  16. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  17. Natural Product Activity and Species Source (NPASS)
  18. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
    2-Hydroxy-3-methylbutyric acid
    https://markerdb.ca/chemicals/230
  19. MassBank Europe
  20. 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
  21. Metabolomics Workbench
  22. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Butanoic acid, 2-hydroxy-3-methyl-
    http://www.nist.gov/srd/nist1a.cfm
  23. NMRShiftDB
  24. Springer Nature
  25. Wikidata
    (RS)-2-hydroxyisovaleric acid
    https://www.wikidata.org/wiki/Q27104874
  26. PubChem
  27. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  28. GHS Classification (UNECE)
  29. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  30. The Natural Products Atlas
    LICENSE
    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  31. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  32. PATENTSCOPE (WIPO)
  33. NCBI
CONTENTS