Chemistry:Valeric acid

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Short description: Carboxylic acid – CH3(CH2)3COOH
Not to be confused with Valerenic acid.
Valeric acid[1]
Valeric acid
Names
IUPAC name
Pentanoic acid
Systematic IUPAC name
Pentanoic acid
Other names
  • 1-Butanecarboxylic acid
  • Propylacetic acid
  • n-Pentanoic acid
  • Valerianic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • Valeric acid: 203-677-2
RTECS number
  • Valeric acid: YV6100000
UNII
UN number 3265
Properties
CH
3(CH
2)
3COOH
Molar mass 102.133 g·mol−1
Appearance Colorless liquid
Odor Cheesy, acidic, rancid[2]
Density 0.930 g/cm3
Melting point −34.5 °C (−30.1 °F; 238.7 K)
Boiling point 185 °C (365 °F; 458 K)
4.0 g/100 mL (20 °C (68 °F))
log P 1.8[3]
Vapor pressure 0.3 hPa (0.0044 psi) (20 °C (68 °F))[3]
Acidity (pKa) 4.82
−66.85×10−6 cm3/mol
1.408[2]
Viscosity 2.2 mPa·s (20 °C (68 °F))[3]
Hazards
GHS pictograms GHS05: Corrosive
GHS Signal word Danger
H227, H314, H412
P210, P264, P273, P280, P301+330+331, P303+361+353, P304+340+310, P305+351+338+310, P363, P370+378, P403+235, P405, P501
NFPA 704 (fire diamond)
Flash point 86 °C (187 °F; 359 K)[3]
440 °C (824 °F; 713 K)[3]
Explosive limits 1.6% to 7.6%[2]
Lethal dose or concentration (LD, LC):
  • 4600 mg/kg (oral, rat)
  • >2 g/kg (dermal, rat)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH
3(CH
2)
3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

History

Valeric acid is a minor constituent of the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. It was first isolated in the 19th century.[4] The dried root of this plant has been used medicinally since antiquity.[5] The related isovaleric acid shares its unpleasant odor and their chemical identity was investigated by oxidation of the components of fusel alcohol, which includes the five-carbon amyl alcohols.[6] Valeric acid is one volatile component in swine manure. Other components include other carboxylic acids, skatole, trimethyl amine, and isovaleric acid.[7] It is also a flavor component in some foods.[8]

Manufacture

In industry, valeric acid is produced by the oxo process from 1-butene and syngas, forming pentanal, which is oxidised to the final product.[9]

H
2 + CO + CH
3CH
2CHCH
2 → CH
3(CH
2)
3CHO → CH
3(CH
2)
3COOH

It can also be produced from biomass-derived sugars via levulinic acid and this alternative has received considerable attention as a way to produce biofuels.[10][11]

Valeric acid can also be prepared by oxidizing 1-pentanol with potassium permanganate according to the following reaction:[citation needed]

CH
3(CH
2)
4OH + KMnO
4 + H
2SO
4 → CH
3(CH
2)
3COOH + MnSO
4 + K
2SO
4 + H
2O

Reactions

Valeric acid reacts as a typical carboxylic acid: it can form amide, ester, anhydride, and chloride derivatives.[12] The latter, valeryl chloride is commonly used as the intermediate to obtain the others.

Uses

Valeric acid occurs naturally in some foods but is also used as a food additive.[13] Its safety in this application was reviewed by an FAO and WHO panel, who concluded that there were no safety concerns at the likely levels of intake.[14] The compound is used for the preparation of derivatives, notably its volatile esters which, unlike the parent acid, have pleasant odors and fruity flavors and hence find applications in perfumes, cosmetics and foodstuffs.[9] Typical examples are the methyl valerates, ethyl valerates, and pentyl valerates.[15][16][17]

Biology

In humans, valeric acid is a minor product[18] of the gut microbiome and can also be produced by metabolism of its esters found in food.[19] The restoration of levels of this acid in the gut has been suggested as the mechanism that results in control of Clostridioides difficile infection after fecal microbiota transplant.[20]

Valerate has been found to act as a histone deacetylase (HDAC) inhibitor[21][22][23] and may act as a biased agonist of the GABAB receptor.[24] It has been found to increase γ-aminobutyric acid (GABA) levels in feces, blood, and brain in rodents.[25] The mechanism of this effect is unknown.[25] However, valeric acid is structurally similar to valproic acid, which is known to act as a GABA transaminase (GABA-T) inhibitor, though valeric acid has yet to be assessed at this potential target.[25]

Valerate salts and esters

The valerate, or pentanoate, ion is C
4H
9COO−
, the conjugate base of valeric acid. It is the form found in biological systems at physiological pH. A valerate, or pentanoate, compound is a carboxylate salt or ester of valeric acid. Many steroid-based pharmaceuticals, for example ones based on betamethasone or hydrocortisone, include the steroid as the valerate ester.

Examples

See also

References

  1. ↑ Budavari, Susan, ed. (2001), An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.), Merck, p. 1764, ISBN 0911910131 
  2. ↑ 2.0 2.1 2.2 2.3 Sigma-Aldrich. "Valeric acid". https://www.sigmaaldrich.com/catalog/product/aldrich/W310107?lang=en&region=GB. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "SDS - Valeric acid". Ward Hill, MA, USA: ThermoFisher Scientific. 21 December 2025. https://www.fishersci.com/store/msds?partNumber=AAA16238AE&productDescription=VALERIC+ACID+100ML&vendorId=VN00024248&countryCode=US&language=en. 
  4. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named EB1911
  5. ↑ Patočka, Jiří; Jakl, Jiří (2010). "Biomedically relevant chemical constituents of Valeriana officinalis". Journal of Applied Biomedicine 8: 11–18. doi:10.2478/v10136-009-0002-z. 
  6. ↑ Pedler, Alexander (1868). "On the isomeric forms of valeric acid". Journal of the Chemical Society 21: 74–76. doi:10.1039/JS8682100074. https://zenodo.org/record/2175638. 
  7. ↑ Ni, Ji-Qin; Robarge, Wayne P.; Xiao, Changhe; Heber, Albert J. (2012). "Volatile organic compounds at swine facilities: A critical review". Chemosphere 89 (7): 769–788. doi:10.1016/j.chemosphere.2012.04.061. PMID 22682363. Bibcode: 2012Chmsp..89..769N. 
  8. ↑ Wang, Pao-Shui; Kato, Hiromichi; Fujimaki, Masao (1970). "Studies on Flavor Components of Roasted Barley". Agricultural and Biological Chemistry 34 (4): 561–567. doi:10.1080/00021369.1970.10859653. 
  9. ↑ 9.0 9.1 Riemenschneider, Wilhelm (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. 
  10. ↑ Lange, Jean-Paul; Price, Richard; Ayoub, Paul M.; Louis, Jurgen; Petrus, Leo; Clarke, Lionel; Gosselink, Hans (2010). "Valeric Biofuels: A Platform of Cellulosic Transportation Fuels". Angewandte Chemie International Edition 49 (26): 4479–4483. doi:10.1002/anie.201000655. PMID 20446282. Bibcode: 2010ACIE...49.4479L. 
  11. ↑ Yan, Long; Yao, Qian; Fu, Yao (2017). "Conversion of levulinic acid and alkyl levulinates into biofuels and high-value chemicals". Green Chemistry 19 (23): 5527–5547. doi:10.1039/C7GC02503C. 
  12. ↑ Jenkins, P. R. (1985). "Carboxylic acids and derivatives". General and Synthetic Methods. 7. pp. 96–160. doi:10.1039/9781847556196-00096. ISBN 978-0-85186-884-4. 
  13. ↑ Shahidi, Fereidoon; Rubin, Leon J.; d'Souza, Lorraine A.; Teranishi, Roy; Buttery, Ron G. (1986). "Meat flavor volatiles: A review of the composition, techniques of analysis, and sensory evaluation". CRC Critical Reviews in Food Science and Nutrition 24 (2): 141–243. doi:10.1080/10408398609527435. PMID 3527563. 
  14. ↑ FAO/WHO Expert Committee on food additives (1998). "Safety evaluation of certain food additives and contaminants". http://www.inchem.org/documents/jecfa/jecmono/v040je10.htm. 
  15. ↑ "Methyl valerate". http://www.thegoodscentscompany.com/data/rw1008901.html. 
  16. ↑ "Ethyl valerate". http://www.thegoodscentscompany.com/data/rw1000701.html. 
  17. ↑ "Amyl valerate". http://www.thegoodscentscompany.com/data/rw1005951.html. 
  18. ↑ Markowiak-Kopeć, Paulina; Śliżewska, Katarzyna (2020). "The Effect of Probiotics on the Production of Short-Chain Fatty Acids by Human Intestinal Microbiome". Nutrients 12 (4): 1107. doi:10.3390/nu12041107. PMID 32316181. 
  19. ↑ "Metabocard for Valeric acid". 2020-04-23. https://hmdb.ca/metabolites/HMDB0000892. 
  20. ↑ McDonald, Julie A.K.; Mullish, Benjamin H.; Pechlivanis, Alexandros; Liu, Zhigang; Brignardello, Jerusa; Kao, Dina; Holmes, Elaine; Li, Jia V. et al. (2018). "Inhibiting Growth of Clostridioides difficile by Restoring Valerate, Produced by the Intestinal Microbiota". Gastroenterology 155 (5): 1495–1507.e15. doi:10.1053/j.gastro.2018.07.014. PMID 30025704. 
  21. ↑ "Molecular Targets of Valeric Acid: A Bioactive Natural Product for Endocrine, Metabolic, and Immunological Disorders". Endocr Metab Immune Disord Drug Targets 24 (13): 1506–1517. 2024. doi:10.2174/0118715303262653231120043819. PMID 38375842. 
  22. ↑ "Valeric Acid Suppresses Liver Cancer Development by Acting as a Novel HDAC Inhibitor". Mol Ther Oncolytics 19: 8–18. December 2020. doi:10.1016/j.omto.2020.08.017. PMID 33024815. 
  23. ↑ "Human gut bacteria as potent class I histone deacetylase inhibitors in vitro through production of butyric acid and valeric acid". PLOS ONE 13 (7). 2018. doi:10.1371/journal.pone.0201073. PMID 30052654. Bibcode: 2018PLoSO..1301073Y. 
  24. ↑ "Activation of GABBR1 by New Ligand Valerate Transcriptionally Regulates ATF4-NRF2-CXCL13 Axis Mediating CD8+ T Cell Anti-Tumor Immunity". Int J Biol Sci 22 (9): 4496–4516. 2026. doi:10.7150/ijbs.127859. PMID 42157924. 
  25. ↑ 25.0 25.1 25.2 "Short-chain fatty acid valerate reduces voluntary alcohol intake in male mice". Microbiome 12 (1). June 2024. doi:10.1186/s40168-024-01829-6. PMID 38886761. 

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