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| Names | |
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| IUPAC name Pentanoic acid | |
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| ChemSpider | |
| ECHA InfoCard | 100.003.344 |
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| 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: | |
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| Danger | |
| H314,H412 | |
| P273,P280,P303+P361+P353,P305+P351+P338+P310 | |
| NFPA 704 (fire diamond) | |
| 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 acid orpentanoic acid is a straight-chainalkylcarboxylic acid with 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.Salts andesters of valeric acid are known asvalerates orpentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, includingethyl valerate andpentyl valerate are used asfood additives because of their fruity flavors.
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 acid shares 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]
In industry, valeric acid is produced by theoxo process from1-butene andsyngas, formingvaleraldehyde, which isoxidised to the final product.[8]
It can also be produced from biomass-derived sugars vialevulinic acid and this alternative has received considerable attention as a way to producebiofuels.[9][10]
Valeric acid reacts as a typical carboxylic acid: it can formamide,ester,anhydride, andchloride derivatives.[11] The latter,valeryl chloride is commonly used as the intermediate to obtain the others.
Valeric acid occurs naturally in some foods but is also used as a food additive.[12] Its safety in this application was reviewed by anFAO andWHO 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 volatileesters which, 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]
In humans, valeric acid is a minor product[17] of thegut 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 ofClostridioides difficile infection afterfecal microbiota transplant.[19]
Thevalerate, orpentanoate,ion isC4H9COO−, theconjugate base of valeric acid. It is the form found in biological systems atphysiological pH. A valerate, or pentanoate, compound is acarboxylate salt or ester of valeric acid.Manysteroid-basedpharmaceuticals, for example ones based onbetamethasone orhydrocortisone, include the steroid as the valerate ester.
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