Valeric acid methyl ester

Structural formula
General
Surname	Valeric acid methyl ester
other names	Methyl pentanoate; Methyl pentanoate ( IUPAC ); Validol;
Molecular formula	C 6 H 12 O 2
Brief description	colorless liquid
External identifiers / databases
EC number	210-838-0
ECHA InfoCard	100,009,853
PubChem	12206
Wikidata	Q388740
properties
Molar mass	116.16 g mol −1
density	0.88 g cm −3
Melting point	−91 ° C
boiling point	126-128 ° C
Vapor pressure	18.6 h Pa (30 ° C); 32.0 hPa (40 ° C); 52.8 hPa (50 ° C);
solubility	poor in water (5 g l −1 at 25 ° C)
Refractive index	1.4003 (20 ° C)
safety instructions
H and P phrases	H: 226-317
	P: 210-280-302 + 352-333 + 313-501
Toxicological data	6600 g m −3 ( LC 50 , mouse , inh. )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Methyl Pentanoate (according to IUPAC methylpentanoate , methyl valerate ) is the ester of valeric acid with the alcohol methanol . The colorless, flammable liquid has a fruity smell and is therefore used as a flavoring , also for food .

Occurrence

Methyl pentanoate is found in essential oils of some plants. The ester is found in small quantities in ripe pineapples and jackfruit .

Presentation and extraction

The technical production takes place through an acid-catalyzed esterification of valeric acid with methanol:

{\ displaystyle \ mathrm {C_ {4} H_ {7} COOH \ + \ CH_ {3} OH {\ xrightarrow [{- H_ {2} O}] {(H_ {3} O ^ {+})}} \ C_ {4} H_ {7} COOCH_ {3}}}

properties

Methyl valerate is a colorless liquid that boils at 127 ° C under normal pressure . The heat of vaporization at the boiling point is 38.01 kJ mol ⁻¹ . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in torr, T in ° C) with A = 6.97357, B = 1463.1497 and C = 220.647 in the temperature range from 24.29 to 165.23 ° C. The ester forms highly flammable vapor-air mixtures. The compound has a flash point of 27 ° C. The ignition temperature is 420 ° C. The substance therefore falls into temperature class T2.

use

The ester has been used as a mild sedative since the 16th century, sometimes as a mixture of validolum with camphor ; Since the 19th century, the validol was also used as a remedy for seasickness.

Today most of the methyl valerate produced is used as a fragrance in the perfume industry.

In organic synthesis, the compound is used in nucleophilic substitutions, in α-alkylations, in heterocycle syntheses and the Kulinkovich reaction .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Entry on methyl valerate in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f Entry on pentanoates. In: Römpp Online . Georg Thieme Verlag, accessed on April 23, 2018.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-364.
↑ Toxicometric parameter of Industrial Toxic Chemicals Under single exposure. Izmerov, NF, et al., Moscow, Center of International Projects, GKNT, Pg. 88, 1982.
↑ Decision 2002/113 / EG of the Commission, p. 72, FL-No: 09.18
↑ J. Schormüller: Handbuch der Lebensmittelchemie. Springer-Verlag, 1965
^ A. Täufel, W. Ternes, L. Tunger, M. Zobel (eds.): Food lexicon. Behr's Verlag, 2005, ISBN 978-3-89947-165-6
^ ^A ^b Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons , 1st Edition Elsevier 2008, ISBN 978-0-8155-1596-8 , p. 333.
↑ Carl L. Yaws: The Yaws Handbook of Vapor Pressure - Antoine Coefficients , 2nd Edition Elsevier 2015, ISBN 978-0-12-802999-2 , p. 39, doi : 10.1016 / B978-0-12-802999-2.00004- 0 .
↑ Note .: Many sources do not distinguish between the Baldriansäuremethylester and similarly acting Baldriansäurementhylester , the ester of valeric acid with menthol .
↑ Central Pharmaceutical Hall for Germany. Theodor Steinkopff, 1914, notes: from 55 1914
↑ Archives for Ship and Tropical Hygiene. 1906, notes: v.10 1906
↑ Excerpta Medica. C. Sallmann., 1904, notes: v.13 1903/1904

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Entry on methyl valerate in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[Roempp-2] ↑ ^a ^b ^c ^d ^e ^f Entry on pentanoates. In: Römpp Online . Georg Thieme Verlag, accessed on April 23, 2018.

[CRC90_3_364-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-364.

[toxp-4] Toxicometric parameter of Industrial Toxic Chemicals Under single exposure. Izmerov, NF, et al., Moscow, Center of International Projects, GKNT, Pg. 88, 1982.

[5] Decision 2002/113 / EG of the Commission, p. 72, FL-No: 09.18

[6] J. Schormüller: Handbuch der Lebensmittelchemie. Springer-Verlag, 1965

[7] A. Täufel, W. Ternes, L. Tunger, M. Zobel (eds.): Food lexicon. Behr's Verlag, 2005, ISBN 978-3-89947-165-6

[Yaws1-8] A ^b Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons , 1st Edition Elsevier 2008, ISBN 978-0-8155-1596-8 , p. 333.

[Yaws2-9] Carl L. Yaws: The Yaws Handbook of Vapor Pressure - Antoine Coefficients , 2nd Edition Elsevier 2015, ISBN 978-0-12-802999-2 , p. 39, doi : 10.1016 / B978-0-12-802999-2.00004- 0 .

[10] Note .: Many sources do not distinguish between the Baldriansäuremethylester and similarly acting Baldriansäurementhylester , the ester of valeric acid with menthol .

[11] Central Pharmaceutical Hall for Germany. Theodor Steinkopff, 1914, notes: from 55 1914

[12] Archives for Ship and Tropical Hygiene. 1906, notes: v.10 1906

[13] Excerpta Medica. C. Sallmann., 1904, notes: v.13 1903/1904