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Valeric acid

From Wikipedia, the free encyclopedia
Not to be confused withValerenic acid.
Valeric acid[1]
Valeric acid
Names
IUPAC name
Pentanoic acid
Other names
1-Butanecarboxylic acid
Propylacetic acid
C5:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.344Edit this at Wikidata
EC Number
  • Valeric acid: 203-677-2
RTECS number
  • Valeric acid: YV6100000
UNII
  • InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)checkY
    Key: NQPDZGIKBAWPEJ-UHFFFAOYSA-NcheckY
  • Valeric acid: InChI=1/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)
    Key: NQPDZGIKBAWPEJ-UHFFFAOYAU
  • Valeric acid: CCCCC(O)=O
Properties
C5H10O2
Molar mass 102.133g·mol−1
Appearance Colorless liquid
Density 0.930 g/cm3
Melting point −34.5 °C (−30.1 °F; 238.7 K)
Boiling point 185 °C (365 °F; 458 K)
4.97 g/100 mL
Acidity(pKa) 4.82
-66.85·10−6cm3/mol
Hazards[2]
GHSlabelling:
GHS05: Corrosive
Danger
H314,H412
P273,P280,P303+P361+P353,P305+P351+P338+P310
NFPA 704(fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 86 °C (187 °F; 359 K)
Related compounds
Related compounds
 Butyric acid,Hexanoic acid
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Valeric acidorpentanoic acidis a straight-chainalkylcarboxylic acidwith thechemical formulaCH3(CH2)3COOH.Like other low-molecular-weight carboxylic acids, it has anunpleasant odor.It is found in the perennial flowering plantValeriana officinalis,from which it gets its name. Its primary use is in the synthesis of itsesters.Saltsandestersof valeric acid are known asvaleratesorpentanoates.Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, includingethyl valerateandpentyl valerateare used asfood additivesbecause of their fruity flavors.

History[edit]

Valeric acid is a minor constituent of the perennial flowering plantvalerian(Valeriana officinalis), from which it gets its name.[3]The dried root of this plant has been used medicinally since antiquity.[4]The relatedisovaleric acidshares its unpleasant odor and their chemical identity was investigated by oxidation of the components offusel alcohol,which includes the five-carbonamyl alcohols.[5] Valeric acid is one volatile component in swine manure. Other components include other carboxylic acids,skatole,trimethyl amine,andisovaleric acid.[6]It is also a flavor component in some foods.[7]

Manufacture[edit]

In industry, valeric acid is produced by theoxo processfrom1-buteneandsyngas,formingvaleraldehyde,which isoxidisedto the final product.[8]

H2+ CO + CH3CH2CH=CH2→ CH3CH2CH2CH2CHO →valeric acid

It can also be produced from biomass-derived sugars vialevulinic acidand this alternative has received considerable attention as a way to producebiofuels.[9][10]

Reactions[edit]

Valeric acid reacts as a typical carboxylic acid: it can formamide,ester,anhydride,andchloridederivatives.[11]The latter,valeryl chlorideis commonly used as the intermediate to obtain the others.

Uses[edit]

Valeric acid occurs naturally in some foods but is also used as a food additive.[12]Its safety in this application was reviewed by anFAOandWHOpanel, who concluded that there were no safety concerns at the likely levels of intake.[13]The compound is used for the preparation of derivatives, notably its volatileesterswhich, unlike the parent acid, have pleasant odors and fruity flavors and hence find applications in perfumes, cosmetics and foodstuffs.[8]Typical examples are themethyl valerates,[14]ethyl valerates,[15]andpentyl valerates.[16]

Biology[edit]

In humans, valeric acid is a minor product[17]of thegut microbiomeand can also be produced by metabolism of its esters found in food.[18]The restoration of levels of this acid in the gut has been suggested as the mechanism that results in control ofClostridioides difficileinfectionafterfecal microbiota transplant.[19]

Valerate salts and esters[edit]

Thevalerate,orpentanoate,ionisC4H9COO−,theconjugate baseof valeric acid. It is the form found in biological systems atphysiological pH.A valerate, or pentanoate, compound is acarboxylate saltor ester of valeric acid. Manysteroid-basedpharmaceuticals,for example ones based onbetamethasoneorhydrocortisone,include the steroid as the valerate ester.

Examples[edit]

See also[edit]

Look upvaleric acidin Wiktionary, the free dictionary.

References[edit]

  1. ^Merck Index,13th Edition, 2001, page 1764.
  2. ^Sigma-Aldrich."Valeric acid".Retrieved2020-09-29.
  3. ^Chisholm, Hugh,ed. (1911)."Valeric Acid".Encyclopædia Britannica.Vol. 27 (11th ed.). Cambridge University Press. p. 859.
  4. ^Patočka, Jiří; Jakl, Jiří (2010)."Biomedically relevant chemical constituents ofValeriana officinalis".Journal of Applied Biomedicine.8:11–18.doi:10.2478/v10136-009-0002-z.
  5. ^Pedler, Alexander (1868)."On the isomeric forms of valeric acid".Journal of the Chemical Society.21:74–76.doi:10.1039/JS8682100074.
  6. ^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.Bibcode:2012Chmsp..89..769N.doi:10.1016/j.chemosphere.2012.04.061.PMID22682363.
  7. ^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.
  8. ^abRiemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a05_235.ISBN978-3527306732.
  9. ^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.PMID20446282.
  10. ^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.
  11. ^Jenkins, P. R. (1985). "Carboxylic acids and derivatives".General and Synthetic Methods.Vol. 7. pp. 96–160.doi:10.1039/9781847556196-00096.ISBN978-0-85186-884-4.
  12. ^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.PMID3527563.
  13. ^FAO/WHO Expert Committee on food additives (1998)."Safety evaluation of certain food additives and contaminants".Retrieved2020-09-30.
  14. ^"Methyl valerate".The Good Scents Company.Retrieved2020-09-30.
  15. ^"Ethyl valerate".The Good Scents Company.Retrieved2020-09-30.
  16. ^"Amyl valerate".The Good Scents Company.Retrieved2020-09-30.
  17. ^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.PMC7230973.PMID32316181.S2CID216075062.
  18. ^"Metabocard for Valeric acid".Human Metabolome Database.2020-04-23.Retrieved2020-09-30.
  19. ^McDonald, Julie A.K.; Mullish, Benjamin H.; Pechlivanis, Alexandros; Liu, Zhigang; Brignardello, Jerusa; Kao, Dina; Holmes, Elaine; Li, Jia V.; Clarke, Thomas B.; Thursz, Mark R.; Marchesi, Julian R. (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.PMC6347096.PMID30025704.
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