Valeric acid

Source: Wikipedia, the free encyclopedia.
Not to be confused with Valerenic 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
 100.003.344 Edit this at Wikidata
EC Number
  • Valeric acid: 203-677-2
IUPHAR/BPS
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-N checkY
  • 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 102.133 g·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
-66.85·10−6 cm3/mol
Hazards[2]
GHS labelling:
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
Hexanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Valeric acid or pentanoic acid is a straight-chain

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.[3] The dried root of this plant has been used medicinally since antiquity.[4] 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.[5] Valeric acid is one volatile component in swine manure. Other components include other carboxylic acids,

isovaleric acid.[6] It is also a flavor component in some foods.[7]

Manufacture

In industry, valeric acid is produced by the

oxidised to the final product.[8]

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

It can also be produced from biomass-derived sugars via

biofuels.[9][10]

Reactions

Valeric acid reacts as a typical carboxylic acid: it can form

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.

pentyl valerates.[16]

Biology

In humans, valeric acid is a minor product

gut microbiome and 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 of Clostridioides difficile infection after fecal microbiota transplant.[19]

Valerate salts and esters

The valerate, or pentanoate,

carboxylate salt
or ester of valeric acid. Many
pharmaceuticals, for example ones based on betamethasone or hydrocortisone
, include the steroid as the valerate ester.

Examples

See also

Look up valeric acid in Wiktionary, the free dictionary.

References

  1. ^ Merck Index, 13th Edition, 2001, page 1764.
  2. ^ Sigma-Aldrich. "Valeric acid". Retrieved 2020-09-29.
  3. ^ Chisholm, Hugh, ed. (1911). "Valeric Acid" . Encyclopædia Britannica. Vol. 27 (11th ed.). Cambridge University Press. p. 859.
  4. doi:10.2478/v10136-009-0002-z
    .
  5. doi:10.1039/JS8682100074
    .
  6. PMID 22682363
    .
  7. doi:10.1080/00021369.1970.10859653
    .
  8. ^
    ISBN 978-3527306732
    .
  9. PMID 20446282
    .
  10. doi:10.1039/C7GC02503C
    .
  11. ISBN 978-0-85186-884-4
    .
  12. PMID 3527563
    .
  13. ^ FAO/WHO Expert Committee on food additives (1998). "Safety evaluation of certain food additives and contaminants". Retrieved 2020-09-30.
  14. ^ "Methyl valerate". The Good Scents Company. Retrieved 2020-09-30.
  15. ^ "Ethyl valerate". The Good Scents Company. Retrieved 2020-09-30.
  16. ^ "Amyl valerate". The Good Scents Company. Retrieved 2020-09-30.
  17. S2CID 216075062
    .
  18. ^ "Metabocard for Valeric acid". Human Metabolome Database. 2020-04-23. Retrieved 2020-09-30.
  19. PMID 30025704
    .
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