Valeric acid

Last updated
Valeric acid [1]
Valeric acid acsv.svg
Valeric-acid-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • Valeric acid:203-677-2
PubChem CID
RTECS number
  • Valeric acid:YV6100000
UNII
  • InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7) Yes check.svgY
    Key: NQPDZGIKBAWPEJ-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceColorless 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:
GHS-pictogram-acid.svg
Danger
H314, H412
P273, P280, P303+P361+P353, P305+P351+P338+P310
NFPA 704 (fire diamond)
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 their standard state (at 25 °C [77 °F], 100 kPa).

Valeric 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 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.

Contents

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, skatole, trimethyl amine, and isovaleric acid. [6] It is also a flavor component in some foods. [7]

Manufacture

In industry, valeric acid is produced by the oxo process from 1-butene and syngas, forming valeraldehyde, which is oxidised to the final product. [8]

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

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. [9] [10]

Reactions

Valeric acid reacts as a typical carboxylic acid: it can form amide, ester, anhydride, and chloride derivatives. [11] 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. [12] 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. [13] 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. [8] Typical examples are the methyl valerates, [14] ethyl valerates, [15] and pentyl valerates. [16]

Biology

In humans, valeric acid is a minor product [17] of the 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, ion is C 4 H 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

Related Research Articles

<span class="mw-page-title-main">Ester</span> Acid molecule with –OH group(s) replaced by –O–R groups. Chalcogen analogs (S, Se, Te, Po) are included.

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Chalcogen analogues are included. By some authors, organyl derivatives of acidic hydrogen of other acids are called esters as well, but those compounds do not belong to the class "esters" proper, according to the IUPAC. An example of an ester formation is the substitution reaction of a carboxylic acid and an alcohol (R'OH), forming an ester, where R and R′ denote organyl groups, or H in the case of R. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters can be formed from oxoacids, but also from acids that do not contain oxygen.

<span class="mw-page-title-main">Valerian (herb)</span> Species of flowering plant in the honeysuckle family Caprifoliaceae

Valerian is a perennial flowering plant native to Europe and Asia. In the summer when the mature plant may have a height of 1.5 metres, it bears sweetly scented pink or white flowers that attract many fly species, especially hoverflies of the genus Eristalis. It is consumed as food by the larvae of some Lepidoptera species, including the grey pug.

<span class="mw-page-title-main">Isobutyric acid</span> Carboxylic acid with chemical formula (CH3)2CHCO2H

Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH. It is an isomer of n-butyric acid. It is classified as a short-chain fatty acid. Deprotonation or esterification gives derivatives called isobutyrates.

<span class="mw-page-title-main">Levulinic acid</span> Chemical compound

Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH3C(O)CH2CH2CO2H. It is classified as a keto acid. This white crystalline solid is soluble in water and polar organic solvents. It is derived from degradation of cellulose and is a potential precursor to biofuels, such as ethyl levulinate.

Enanthic acid, also called heptanoic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid functional group. It is a colorless oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether. Salts and esters of enanthic acid are called enanthates or heptanoates.

<span class="mw-page-title-main">3-Methylbutanoic acid</span> Carboxylic acid with chemical formula (CH3)2CHCH2CO2H CH3CH2

3-Methylbutanoic acid, also known as β-methylbutyric acid or more commonly isovaleric acid, is a branched-chain alkyl carboxylic acid with the chemical formula (CH3)2CHCH2CO2H. It is classified as a short-chain fatty acid. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.

<span class="mw-page-title-main">Ethyl pentanoate</span> Chemical compound

Ethyl pentanoate, also commonly known as ethyl valerate, is an organic compound used in flavors. It is an ester with the molecular formula C7H14O2. This colorless liquid is poorly soluble in water but miscible with organic solvents.

<span class="mw-page-title-main">Methyl pentanoate</span> Chemical compound

Methyl pentanoate, commonly known as methyl valerate, is the methyl ester of pentanoic acid with a fruity odor.

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">Ethyl propionate</span> Chemical compound

Ethyl propionate is an organic compound with formula C2H5O2CCH2CH3. It is the ethyl ester of propionic acid. It is a colorless volatile liquid with a pineapple-like odor. Some fruits such as kiwis and strawberries contain ethyl propionate in small amounts.

<i>tert</i>-Butylthiol Chemical compound

tert-Butylthiol, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol is used as an odorant for natural gas, which is otherwise odorless. It may also have been used as a flavoring agent.

<span class="mw-page-title-main">4-Methylcyclohexanemethanol</span> Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

<span class="mw-page-title-main">GABA analogue</span> Class of drugs

A GABA analogue is a compound which is an analogue or derivative of the neurotransmitter gamma-Aminobutyric acid (GABA).

Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and ethanol. A colorless liquid at room temperature, it has the semi-developed formula of CH3(CH2)6COOCH2CH3, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers. It is used in the creation of synthetic fruity scents.

<span class="mw-page-title-main">Ethyl isovalerate</span> Chemical compound

Ethyl isovalerate is an organic compound that is the ester formed from ethyl alcohol and isovaleric acid. It has a fruity odor and flavor and is used in perfumery and as a food additive.

2-Methylbutanoic acid, also known as 2-methylbutyric acid is a branched-chain alkyl carboxylic acid with the chemical formula CH3CH2CH(CH3)CO2H, classified as a short-chain fatty acid. It exists in two enantiomeric forms, (R)- and (S)-2-methylbutanoic acid. (R)-2-methylbutanoic acid occurs naturally in cocoa beans and (S)-2-methylbutanoic occurs in many fruits such as apples and apricots, as well as in the scent of the orchid Luisia curtisii.

Methyl hexanoate is the fatty acid methyl ester of hexanoic acid, a colourless liquid organic compound with the chemical formula CH3−(CH2)4−COO−CH3. It is found naturally in many foods and has a role as a plant metabolite. It can also be found in the cytoplasm of cells.

Pentenoic acid is any of five mono-carboxylic acids whose molecule has an unbranched chain of five carbons connected by three single bonds and one double bond. That is, any compound with one of the formulas HO(O=)C−CH=CH−CH2−CH3 (2-pentenoic), HO(O=)C−CH2−CH=CH−CH3 (3-pentenoic), or HO(O=)C−CH2−CH2−CH=CH2 (4-pentenoic). In the IUPAC-recommended nomenclature, these acids are called pent-2-enoic, pent-3-enoic, and pent-4-enoic, respectively. All these compounds have the empirical formula C
5H
8O
2.

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. ↑ 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 .
  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. PMID   22682363.
  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. 1 2 Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235.
  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 . PMID   20446282.
  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. ISBN   978-0-85186-884-4.
  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. 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. ↑ 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 . PMC   7230973 . PMID   32316181. S2CID   216075062.
  18. ↑ "Metabocard for Valeric acid". Human Metabolome Database. 2020-04-23. Retrieved 2020-09-30.
  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. PMC   6347096 . PMID   30025704.
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