Valeric acid

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Valeric acid
Image:Valeric acid.png
IUPAC name	Pentanoic acid
Other names	Valeric acid Butane-1-carboxylic acid
Identifiers
CAS number	109-52-4
RTECS number	YV6100000
SMILES	CCCCC(O)=O
Properties
Molecular formula	C5H10O2
Molar mass	102.13 g/mol
Appearance	colorless liquid
Density	0.930 g/cm³, liquid
Melting point	-34.5 °C
Boiling point	186-187 °C
Solubility in water	4.97 g/100 ml (25 °C)
Acidity (pKa)	4.82
Hazards
Main hazards	irritant
R-phrases	34 52/53
S-phrases	26 36 45 61
Flash point	86 °C
Related Compounds
Related compounds	Butyric acid Ethyl valerate Pentyl pentanoate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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 a very unpleasant odor similar to that of dirty socks. It is found naturally in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Its primary use is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

Valeric acid has a similar structure to both GHB and the neurotransmitter GABA. It differs from valproic acid (Depakene) simply by lacking a 3-carbon side chain.

Safety

Valeric acid can cause irritation to humans if it comes into contact with the skin or eyes, but otherwise causes little harm because it tends not to vapourise at room temperature unless it is in its pure glacial form. It is, however, toxic to aquatic life and so should not be disposed of into drains without first diluting the acidic solution.

Practical Applications

Valerian root has a long history of use as an herbal sedative/hypnotic.

Valeric acid, if applied directly, has been claimed to be an effective treatment for acne, as yet without support from peer reviewed trials.

See also

• Valproic acid
• Pivalic acid (2,2-dimethylpropanoic acid)

References

bg:Валерианова киселина cs:Kyselina valerová de:Valeriansäure eo:Valerata acido lv:Baldriānskābe hu:Valeriánsav nl:Valeriaanzuurfi:Valeriaanahappo sv:Valeriansyra