Valeric acid (CHEM003563)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-09-05 17:12:46 UTC
Update Date2026-03-26 21:21:30 UTC
Accession NumberCHEM003563
Identification
Common NameValeric acid
ClassSmall Molecule
DescriptionValeric acid, or pentanoic acid, is a straight chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low molecular weight carboxylic acids, it has a very unpleasant odor. It is found naturally in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Its primary use is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Cosmetic Toxin
  • Flavouring Agent
  • Food Additive
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Butanecarboxylic acidChEBI
CH3-[CH2]3-COOHChEBI
N-BuCOOHChEBI
N-PentanoateChEBI
N-Pentanoic acidChEBI
N-Valeric acidChEBI
PentanoateChEBI
Pentanoic acidChEBI
Pentoic acidChEBI
Propylacetic acidChEBI
ValerateChEBI
Valerianic acidChEBI
ValeriansaeureChEBI
Valeric acid, normalChEBI
1-ButanecarboxylateGenerator
N-ValerateGenerator
PentoateGenerator
PropylacetateGenerator
ValerianateGenerator
Valerate, normalGenerator
1-PentanoateHMDB
1-Pentanoic acidHMDB
ButanecarboxylateHMDB
Butanecarboxylic acidHMDB
Kyselina valerovaHMDB
N-C4H9COOHHMDB
ValeriansaureHMDB
Valeric acid normalHMDB
N-Pentanoic acid, ammonium saltHMDB
N-Pentanoic acid, potassium saltHMDB
N-Pentanoic acid, sodium saltHMDB
N-Pentanoic acid, zinc saltHMDB
N-Pentanoic acid, maganese (+2) saltHMDB
N-Pentanoic acid, 11C-labeledHMDB
Lithium pentanoateHMDB
N-Pentanoic acid, 11C-labeled sodium saltHMDB
Valeric acidKEGG
Chemical FormulaC5H10O2
Average Molecular Mass102.132 g/mol
Monoisotopic Mass102.068 g/mol
CAS Registry Number109-52-4
IUPAC Namepentanoic acid
Traditional NameN-valeric acid
SMILESCCCCC(O)=O
InChI IdentifierInChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)
InChI KeyNQPDZGIKBAWPEJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Bladder
  • Nervous Tissues
  • Neuron
  • Skin
  • Stratum Corneum
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-34°C
Boiling Point186.1°C
Solubility2.4E+004 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility40.3 g/LALOGPS
logP1.34ALOGPS
logP1.37ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.47 m³·mol⁻¹ChemAxon
Polarizability11.23 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fr-9000000000-5ef705125c3c70ad3df3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9000000000-2160417549a364f722dfSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fr-9000000000-5ef705125c3c70ad3df3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9000000000-2160417549a364f722dfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-317b810c8d610eaf0188Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05dr-9200000000-cfee4e723931c0c4882eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0kdi-9200000000-68de4edfab1763d25290Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-5807dc032b484168ad7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-6815adcb2b82e3f1f29fSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-03fr-9000000000-5ef705125c3c70ad3df3Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03di-9000000000-90144d1440b06340fe7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-99bad9fba8cf3bc081e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-95b1b8722cad92c490e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-2900000000-d6ebac4ebed40b98b291Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0udi-9000000000-94459eb26bcb7c315bcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-e212c5cbe08c4eb40b95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-99bad9fba8cf3bc081e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-95b1b8722cad92c490e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-d6ebac4ebed40b98b291Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-9000000000-94459eb26bcb7c315bcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-e212c5cbe08c4eb40b95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-3900000000-dd2e8ada707700a86c15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9700000000-3b6086e299b180404c66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4u-9100000000-1c4280d0a9143e3d48d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-bc80b097ba0f51c3ca40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-a4de42a48fe44ac339faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9800000000-543e60b2b278c1d51c48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-6b15e313e3ee4ada68aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9100000000-e626913b2548db6c8608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-a5c7e6b5fe910559a628Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-890b839f8e2f9ac3fd83Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-9246123374d3104316a3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02406
HMDB IDHMDB0000892
FooDB IDFDB003230
Phenol Explorer IDNot Available
KNApSAcK IDC00001208
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID110
PDB IDNot Available
Wikipedia LinkValeric acid
Chemspider ID7701
ChEBI ID17418
PubChem Compound ID7991
Kegg Compound IDC00803
YMDB IDYMDB01484
ECMDB IDM2MDB005480
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. Ruiz, Maria Olga; Cabezas, Jose Luis; Escudero, Isabel; Coca, Jose. Valeric acid extraction with tri-n-butyl phosphate impregnated in a macroporous resin: II. Studies in fixed bed columns. Journal of Chemical Technology and Biotechnology (2006), 81(3), 275-281.
2. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.
3. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
4. Ruiz, Maria Olga; Cabezas, Jose Luis; Escudero, Isabel; Coca, Jose. Valeric acid extraction with tri-n-butyl phosphate impregnated in a macroporous resin: II. Studies in fixed bed columns. Journal of Chemical Technology and Biotechnology (2006), 81(3), 275-281.
5. Vuotto ML, Miranda R, Ritieni A, Basile A, Ricciardi L, Di Prisco R, Nicolosi G, Mascolo N: Improvement of (+)-catechin inhibitory activity on human PMN respiratory burst by (+)-3-O-propionyl and (-)-3-O-valeryl substitution. J Pharm Pharmacol. 2003 Mar;55(3):399-405.
6. Nielsen FH, Honore E, Kristoffersen K, Secher NJ, Pedersen GT: Changes in serum lipids during treatment with norgestrel, oestradiol-valerate and cycloprogynon. Acta Obstet Gynecol Scand. 1977;56(4):367-70.
7. Siddiqui O, Roberts MS, Polack AE: Percutaneous absorption of steroids: relative contributions of epidermal penetration and dermal clearance. J Pharmacokinet Biopharm. 1989 Aug;17(4):405-24.
8. Sudo S, Sudo M, Simons CT, Dessirier JM, Carstens E: Sensitization of trigeminal caudalis neuronal responses to intraoral acid and salt stimuli and desensitization by nicotine. Pain. 2002 Aug;98(3):277-86.
9. Punnonen R, Lovgren T, Kouvonen I: Demonstration of estrogen receptors in the skin. J Endocrinol Invest. 1980 Jul-Sep;3(3):217-21.
10. Kuznetsov DD, Alsikafi NF, O'Connor RC, Steinberg GD: Intravesical valrubicin in the treatment of carcinoma in situ of the bladder. Expert Opin Pharmacother. 2001 Jun;2(6):1009-13.
11. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7.
12. Punnonen R, Lovgren T, Kouvonen I: Demonstration of estrogen receptors in the skin. J Endocrinol Invest. 1980 Jul-Sep;3(3):217-21.
13. Kubota K, Maibach HI: In vitro percutaneous permeation of betamethasone and betamethasone 17-valerate. J Pharm Sci. 1993 Oct;82(10):1039-45.
14. Tauber VU: [Percutaneous absorption of diflucortolone valerate in guinea pigs and man (author's transl)]. Arzneimittelforschung. 1976;26(7b):1479-84.
15. Saunders DM, Hunter JC, Shutt DA, O'Neill BJ: The effect of oestradiol valerate therapy on coagulation factors and lipid and oestrogen levels in oophorectomised women. Aust N Z J Obstet Gynaecol. 1978 Aug;18(3):198-201.
16. Abuknesha RA, Luk C: Paraquat enzyme-immunoassays in biological samples: assessment of the effects of hapten-protein bridge structures on assay sensitivity. Analyst. 2005 Jun;130(6):956-63. Epub 2005 Apr 25.
17. Wilbur DS, Hamlin DK, Chyan MK, Kegley BB, Pathare PM: Biotin reagents for antibody pretargeting. 5. Additional studies of biotin conjugate design to provide biotinidase stability. Bioconjug Chem. 2001 Jul-Aug;12(4):616-23.
18. Tauber VU, Amin M, Fuchs P, Speck U: [Comparative studies in man on the percutaneous absorption of diflucortolone valerate, betamethasone-17-valerate, beclomethasone dipropionate and fluocinolone acetonide]. Arzneimittelforschung. 1976;26(7b):1492-5.
19. Lotti M, Moretto A: Promotion of organophosphate induced delayed polyneuropathy by certain esterase inhibitors. Chem Biol Interact. 1999 May 14;119-120:519-24.
20. Jacob TJ, Fraser C, Wang L, Walker V, O'Connor S: Psychophysical evaluation of responses to pleasant and mal-odour stimulation in human subjects; adaptation, dose response and gender differences. Int J Psychophysiol. 2003 Apr;48(1):67-80.
21. Vilska S, Punnonen R, Rauramo L: Long-term post-menopausal hormone therapy and serum HDL-C, total cholesterol and triglycerides. Maturitas. 1983 Aug;5(2):97-104.
22. Bottcher MF, Nordin EK, Sandin A, Midtvedt T, Bjorksten B: Microflora-associated characteristics in faeces from allergic and nonallergic infants. Clin Exp Allergy. 2000 Nov;30(11):1590-6.
23. Gysler A, Kleuser B, Sippl W, Lange K, Korting HC, Holtje HD, Korting HC: Skin penetration and metabolism of topical glucocorticoids in reconstructed epidermis and in excised human skin. Pharm Res. 1999 Sep;16(9):1386-91.
24. Hoverstad T, Fausa O, Bjorneklett A, Bohmer T: Short-chain fatty acids in the normal human feces. Scand J Gastroenterol. 1984 May;19(3):375-81.
25. Yuille S, Reichardt N, Panda S, Dunbar H, Mulder IE: Human gut bacteria as potent class I histone deacetylase inhibitors in vitro through production of butyric acid and valeric acid. PLoS One. 2018 Jul 27;13(7):e0201073. doi: 10.1371/journal.pone.0201073. eCollection 2018.
26. STADTMAN ER, STADTMAN TC, BARKER HA: Tracer experiments on the mechanism of synthesis of valeric and caproic acids by Clostridium kluyveri. J Biol Chem. 1949 Apr;178(2):677-82.
27. Li Y, Dong J, Xiao H, Zhang S, Wang B, Cui M, Fan S: Gut commensal derived-valeric acid protects against radiation injuries. Gut Microbes. 2020 Jan 13:1-18. doi: 10.1080/19490976.2019.1709387.
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=20507156