Valeric acid or pentanoic acid is a straight-chain alkylcarboxylic acid with the chemical formulaCH3(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.
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]
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]
Reactionsedit
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.
Usesedit
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]
^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.
^Pedler, Alexander (1868). "On the isomeric forms of valeric acid". Journal of the Chemical Society. 21: 74–76. doi:10.1039/JS8682100074.
^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.
^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.
^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.
^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.
^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.
^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.
^FAO/WHO Expert Committee on food additives (1998). "Safety evaluation of certain food additives and contaminants". Retrieved 2020-09-30.
^"Methyl valerate". The Good Scents Company. Retrieved 2020-09-30.
^"Ethyl valerate". The Good Scents Company. Retrieved 2020-09-30.
^"Amyl valerate". The Good Scents Company. Retrieved 2020-09-30.
^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. PMID 32316181. S2CID 216075062.
^"Metabocard for Valeric acid". Human Metabolome Database. 2020-04-23. Retrieved 2020-09-30.
^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. PMID 30025704.
January 01, 1970
valeric, acid, confused, with, valerenic, acid, pentanoic, acid, straight, chain, alkyl, carboxylic, acid, with, chemical, formula, 3cooh, like, other, molecular, weight, carboxylic, acids, unpleasant, odor, found, perennial, flowering, plant, valeriana, offic. Not to be confused with Valerenic acid 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 Valeric acid 1 Names IUPAC name Pentanoic acid Other names 1 Butanecarboxylic acidPropylacetic acidC5 0 Lipid numbers Identifiers CAS Number Valeric acid 109 52 4 YValerate 10023 74 2 3D model JSmol Valeric acid Interactive image ChEBI Valeric acid CHEBI 17418Valerate CHEBI 31011 ChEMBL Valeric acid ChEMBL268736 Y ChemSpider Valeric acid 7701 YValerate 102757 ECHA InfoCard 100 003 344 EC Number Valeric acid 203 677 2 IUPHAR BPS Valeric acid 1061 PubChem CID Valeric acid 7991Valerate 114781 RTECS number Valeric acid YV6100000 UNII Valeric acid GZK92PJM7B Y CompTox Dashboard EPA Valeric acid DTXSID7021655 InChI InChI 1S C5H10O2 c1 2 3 4 5 6 7 h2 4H2 1H3 H 6 7 YKey NQPDZGIKBAWPEJ UHFFFAOYSA N YValeric acid InChI 1 C5H10O2 c1 2 3 4 5 6 7 h2 4H2 1H3 H 6 7 Key NQPDZGIKBAWPEJ UHFFFAOYAU SMILES Valeric acid CCCCC O O Properties Chemical formula C 5H 10O 2 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 Solubility in water 4 97 g 100 mL Acidity pKa 4 82 Magnetic susceptibility x 66 85 10 6 cm3 mol Hazards 2 GHS labelling Pictograms Signal word Danger Hazard statements H314 H412 Precautionary statements P273 P280 P303 P361 P353 P305 P351 P338 P310 NFPA 704 fire diamond 310 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 Infobox references Contents 1 History 2 Manufacture 3 Reactions 4 Uses 5 Biology 6 Valerate salts and esters 6 1 Examples 7 See also 8 ReferencesHistory editValeric 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 editIn 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 editValeric 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 editValeric 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 editIn 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 editThe valerate or pentanoate ion is C4H9COO 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 edit Methyl valerate Ethyl valerate Pentyl valerate Betamethasone valerate Estradiol valerate Hydrocortisone valerate Testosterone valerateSee also edit nbsp Look up valeric acid in Wiktionary the free dictionary List of saturated fatty acids List of carboxylic acids 4 Hydroxy 4 methylpentanoic acid Pivalic acid 2 2 dimethylpropanoic acid 3 Methylbutanoic acid also called isovaleric acid Valproic acidReferences edit Merck Index 13th Edition 2001 page 1764 Sigma Aldrich Valeric acid Retrieved 2020 09 29 Chisholm Hugh ed 1911 Valeric Acid Encyclopaedia Britannica Vol 27 11th ed Cambridge University Press p 859 Patocka Jiri Jakl Jiri 2010 Biomedically relevant chemical constituents of Valeriana officinalis Journal of Applied Biomedicine 8 11 18 doi 10 2478 v10136 009 0002 z Pedler Alexander 1868 On the isomeric forms of valeric acid Journal of the Chemical Society 21 74 76 doi 10 1039 JS8682100074 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 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 a b Riemenschneider Wilhelm 2002 Carboxylic Acids Aliphatic Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a05 235 ISBN 978 3527306732 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 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 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 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 FAO WHO Expert Committee on food additives 1998 Safety evaluation of certain food additives and contaminants Retrieved 2020 09 30 Methyl valerate The Good Scents Company Retrieved 2020 09 30 Ethyl valerate The Good Scents Company Retrieved 2020 09 30 Amyl valerate The Good Scents Company Retrieved 2020 09 30 Markowiak Kopec Paulina Slizewska 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 Metabocard for Valeric acid Human Metabolome Database 2020 04 23 Retrieved 2020 09 30 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 Retrieved from https en wikipedia org w index php title Valeric acid amp oldid 1214293309, wikipedia, wiki, book, books, library,
