Butanoic acid, 3-methyl-

Formula: C₅H₁₀O₂
Molecular weight: 102.1317
IUPAC Standard InChI: InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
IUPAC Standard InChIKey: GWYFCOCPABKNJV-UHFFFAOYSA-N
CAS Registry Number: 503-74-2
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: Isovaleric acid; β-Methylbutyric acid; Acetic acid, isopropyl-; Delphinic acid; Isopentanoic acid; Isopropylacetic acid; 3-Methylbutanoic acid; 3-Methylbutyric acid; iso-C4H9COOH; Butyric acid, 3-methyl-; Isovalerianic acid; Kyselina isovalerova; 3-Methyl-n-butyric acid; NSC 62783; Isobutylformic acid; 3-methylbutanoic acid (isovaleric acid); Methylbutanoic acid
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Normal alkane RI, non-polar column, temperature ramp

Go To: Top, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	VF-5 MS	VF-5 MS	HP-5 MS	HP-5 MS	HP-5 MS
Column length (m)	60.	60.	30.	30.	30.
Carrier gas	Helium	Helium	Helium	Helium	Helium
Substrate
Column diameter (mm)	0.32	0.32	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	30.	30.	50.	70.	35.
T_end (C)	260.	260.	240.	290.	195.
Heat rate (K/min)	2.	2.	4.	5.	2.
Initial hold (min)			2.		5.
Final hold (min)	28.	28.	10.	10.	30.
I	867.	872.	837.	817.	845.
Reference	Leffingwell and Alford, 2011	Leffingwell and Alford, 2011	Pino, Marquez, et al., 2010	Radulovic, Dordevic, et al., 2010	Kim and Chung, 2009
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SE-54	HP-5 MS	RTX-5	DB-5	SPB-5
Column length (m)	30.	30.	60.	30.	30.
Carrier gas		Helium		He	He
Substrate
Column diameter (mm)	0.32	0.25	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.25	1.	0.25	0.25
T_start (C)	0.	70.	40.	35.	50.
T_end (C)	200.	290.	205.	220.	250.
Heat rate (K/min)	6.	5.	4.	3.	2.
Initial hold (min)	2.		5.
Final hold (min)		10.	5.	40.
I	875.	827.	838.	831.	840.
Reference	Laselan, Buettner, et al., 2009	Radulovic, Blagojevic, et al., 2009	Berdague, Tournayre, et al., 2007	El-Ghorab A., El-Massry K.F., et al., 2007	Raal, Orav, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	5 % Phenyl methyl siloxane	5 % Phenyl methyl siloxane	DB-5	HP-5MS	HP-5
Column length (m)	30.	30.	25.	30.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.25	0.25
Phase thickness (μm)	1.	1.	0.25	0.25	0.25
T_start (C)	40.	40.	40.	40.	50.
T_end (C)	250.	250.	230.	260.	300.
Heat rate (K/min)	7.	7.	6.	4.	5.
Initial hold (min)	10.	10.	1.		5.
Final hold (min)	5.	5.			5.
I	843.	843.	858.	901.8	864.
Reference	Ramirez R. and Cava R., 2007	Ramirez R. and Cava R., 2007	Zeller and Rychlik, 2007	Zizovic, Stamenic, et al., 2007	Figuérédo, Cabassu, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	BPX5	HP-5	MDN-5	MDN-5
Column length (m)	30.	25.	60.	60.	60.
Carrier gas	Hydrogen	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.20	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.13	0.25	0.25	0.25
T_start (C)	70.	50.	30.	40.	40.
T_end (C)	280.	230.	260.	270.	270.
Heat rate (K/min)	4.	3.	2.	4.	4.
Initial hold (min)	4.	2.	2.	4.	4.
Final hold (min)			28.	5.	5.
I	834.	836.	888.7	878.	855.
Reference	Pino, Marbot, et al., 2006	Boustie, Rapior, et al., 2005	Leffingwell and Alford, 2005	van Loon, Linssen, et al., 2005	van Loon, Linssen, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	HP-5	SE-54	DB-5	SPB-5
Column length (m)	30.	30.	30.	30.	60.
Carrier gas	Helium	Helium	He	H2	Helium
Substrate
Column diameter (mm)	0.32	0.32	0.053	0.25	0.32
Phase thickness (μm)	0.25	0.25	1.5	0.25	1.0
T_start (C)	40.	40.	100.	60.	30.
T_end (C)	250.	250.	250.	280.	230.
Heat rate (K/min)	5.	5.	5.	4.	3.
Initial hold (min)	2.	2.		10.
Final hold (min)	5.	5.		40.
I	873.	878.	820.	830.	828.
Reference	N/A	N/A	Kilic, Hafizoglu, et al., 2004	Pino, Marbot, et al., 2003	Sebastian, Viallon-Fernandez, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5MS	AT-1	DB-5MS	DB-5	HP-5
Column length (m)	30.		30.	30.	60.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.53		0.32	0.32	0.32
Phase thickness (μm)	1.5		0.25	0.25	1.
T_start (C)	40.	50.	40.	40.	40.
T_end (C)	225.	300.	195.	230.	240.
Heat rate (K/min)	6.	10.	5.	6.	3.
Initial hold (min)	5.	2.	5.	2.
Final hold (min)	30.		40.	5.
I	835.	900.	873.	844.	838.
Reference	Cadwallader and Heo, 2001	Kelling, 2001	Suriyaphan, Drake, et al., 2001	Czerny and Grosch, 2000	García, Martín, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	HP-5	OV-101	BP-5
Column length (m)	30.	30.	30.	50.	50.
Carrier gas	H2	H2	He	Nitrogen	He
Substrate
Column diameter (mm)	0.32	0.32	0.25	0.25	0.32
Phase thickness (μm)	0.5	0.5	0.25		1.
T_start (C)	60.	60.	40.	40.	40.
T_end (C)	245.	245.	240.	200.	190.
Heat rate (K/min)	3.	3.	3.	2.	2.
Initial hold (min)	3.	3.	5.	10.	5.
Final hold (min)	20.	20.
I	868.	868.	836.	842.	878.
Reference	Kotseridis and Baumes, 2000	Kotseridis and Baumes, 2000	Novak, Novak, et al., 2000	Tamura, Boonbumrung, et al., 2000	Lopez, Ferreira, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-1	DB-1	SPB-5	Optima 1	HP-1
Column length (m)	25.		50.	25.	25.
Carrier gas			He	Helium
Substrate
Column diameter (mm)	0.20		0.32	0.20	0.32
Phase thickness (μm)			0.25	0.25
T_start (C)	35.	50.	60.	50.	35.
T_end (C)	250.	260.	240.	200.	250.
Heat rate (K/min)	4.	4.	3.	3.	4.
Initial hold (min)
Final hold (min)			20.
I	840.	819.	819.	867.	840.
Reference	Ong and Acree, 1999	Schultz, Kaiser, et al., 1999	Doneanu and Anitescu, 1998	Fons, Rapior, et al., 1998	Ong and Acree, 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BPX-5	DB-5	DB-5	DB-1	DB-1
Column length (m)	50.	60.	60.	60.	60.
Carrier gas	He
Substrate
Column diameter (mm)	0.22	0.32	0.32	0.32
Phase thickness (μm)	0.25	1.	1.
T_start (C)	50.	40.	40.	50.	30.
T_end (C)	250.	200.	200.	230.	200.
Heat rate (K/min)	3.	3.	3.	4.	4.
Initial hold (min)	1.	5.	5.		25.
Final hold (min)	10.	2.	2.	10.	30.
I	843.	838.	842.	830.	830.
Reference	D'Arcy, Rintoul, et al., 1997	Kondjoyan, Viallon, et al., 1997	Kondjoyan, Viallon, et al., 1997	Binder, Benson, et al., 1990	Buttery, Takeoka, et al., 1990
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	DB-1
Column length (m)	60.
Carrier gas	He
Substrate
Column diameter (mm)	0.25
Phase thickness (μm)
T_start (C)	30.
T_end (C)	200.
Heat rate (K/min)	4.
Initial hold (min)	25.
Final hold (min)	5.
I	830.
Reference	Buttery, Teranishi, et al., 1990
Comment	MSDC-RI

References

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes

Leffingwell and Alford, 2011
Leffingwell, J.; Alford, E.D., Volatile constituents of the giant pufball mushroom (Calvatia gigantea), Leffingwell Rep., 2011, 4, 1-17. [all data]

Pino, Marquez, et al., 2010
Pino, J.A.; Marquez, E.; Quijano, C.E.; Castro, D., Volatile compounds in noni (Morinda citrifolia L.) at two ripening stages, Ciencia e Technologia de Alimentos, 2010, 30, 1, 183-187, https://doi.org/10.1590/S0101-20612010000100028 . [all data]

Radulovic, Dordevic, et al., 2010
Radulovic, N.; Dordevic, N.; Markovic, M.; Palic, R., Volatile constituents of Glechoma Hirsuta Waldst. Kit. and G. Hederacea L. (Lamiaceae), Bull. Chem. Soc. Ethiop., 2010, 24, 1, 67-76, https://doi.org/10.4314/bcse.v24i1.52962 . [all data]

Kim and Chung, 2009
Kim, J.-S.; Chung, H.Y., GC-MS analysis of the volatile components in dried boxthorn (Lycium chimensis) Fruit, J. Korean Soc. Appl. Biol. Chem., 2009, 52, 5, 516-524, https://doi.org/10.3839/jksabc.2009.088 . [all data]

Laselan, Buettner, et al., 2009
Laselan, P.; Buettner, A.; Christlbauer, M., Investigation of the retronasal perseption of palm wine (Elaeis guineensis) aroma by application of sensory analysis and exhaled odorant measurement (EXOM), African J. of Food, Agriculture, Nutrition and development, 2009, 9, 2, 793-813. [all data]

Radulovic, Blagojevic, et al., 2009
Radulovic, N.S.; Blagojevic, P.D.; Palic, R.M.; Zlatkovic, B.K.; Stevanovic, B.M., Volatiles from vegetative organs of the paleoendemic resurrection plants Ramonda serbica Panc. and Ramonda nathaliae Panc. at Petrov, J. Serb. Chem. Soc., 2009, 74, 1, 35-44, https://doi.org/10.2298/JSC0901035R . [all data]

Berdague, Tournayre, et al., 2007
Berdague, J.L.; Tournayre, P.; Cambou, S., Novel multi-gas chromatography?olfactometry device and software for the identification of odour-active compounds, J. Chromatogr. A, 2007, 1146, 1, 85-92, https://doi.org/10.1016/j.chroma.2006.12.102 . [all data]

El-Ghorab A., El-Massry K.F., et al., 2007
El-Ghorab A.; El-Massry K.F.; Shibamoto T., Chemical composition of the volatile extract and antioxidant activities of the volatile and nonvolatile extracts of Egyptian corn silk (Zea mays L.), J. Agric. Food Chem., 2007, 55, 22, 9124-9127, https://doi.org/10.1021/jf071646e . [all data]

Raal, Orav, et al., 2007
Raal, A.; Orav, A.; Arak, E.; Kailas, T.; Müürisepp, M., Variation in the composition of the essential oil of Valeriana officinalis L. roots from Estonia, Proc. Est. Acad. Sci. Chem., 2007, 56, 2, 67-74. [all data]

Ramirez R. and Cava R., 2007
Ramirez R.; Cava R., Volatile profiles of dry-cured meat products from three different Iberian x Duroc genotypes, J. Agric. Food Chem., 2007, 55, 5, 1923-1931, https://doi.org/10.1021/jf062810l . [all data]

Zeller and Rychlik, 2007
Zeller, A.; Rychlik, M., Impact of estragole and other odorants on the flavour of anise and tarragon, Flavour Fragr. J., 2007, 22, 2, 105-113, https://doi.org/10.1002/ffj.1765 . [all data]

Zizovic, Stamenic, et al., 2007
Zizovic, I.; Stamenic, M.; Ivanovic, J.; Orlovic, A.; Ristic, M.; Djordjevic, S.; Petrovic, S.D.; Skala, D., Supercritical carbon dioxide extraction of sesquiterpenes from valerian root, J. Supercrit. Fluids, 2007, 43, 2, 249-258, https://doi.org/10.1016/j.supflu.2007.05.007 . [all data]

Figuérédo, Cabassu, et al., 2006
Figuérédo, G.; Cabassu, P.; Chalchat, J.-C.; Pasquier, B., Studies of Mediterranean oregano populations. VIII. Chemical composition of essential oils of oreganos of various origins, Flavour Fragr. J., 2006, 21, 1, 134-139, https://doi.org/10.1002/ffj.1543 . [all data]

Pino, Marbot, et al., 2006
Pino, J.A.; Marbot, R.; Payo, A.; Chao, D.; Herrera, P., Aromatic Plants from Western Cuba VII. Composition of the Leaf Oil of Psidium wrightii KRug et Urb., Lantana involucrata L., Cinnamonum montanum (Sw.) Berchtold et J. Persl. and Caesalpinia violacea (Mill.) Standley, J. Essent. Oil. Res., 2006, 18, 2, 170-174, https://doi.org/10.1080/10412905.2006.9699058 . [all data]

Boustie, Rapior, et al., 2005
Boustie, J.; Rapior, S.; Fortin, H.; Tomas, S.; Bessiere, J.-M., Chemotaxonomic interest of volatile components in Lepista inversa and Lepista flaccida distinctions, Cryptogamie, Mycologie, 2005, 26, 1, 1-4. [all data]

Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D., Volatile constituents of Perique tobacco, Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]

van Loon, Linssen, et al., 2005
van Loon, W.A.M.; Linssen, J.P.H.; Legger, A.; Posthumus, M.A.; Voragen, A.G.J., Identification and olfactometry of French fries flavour extracted at mouth conditions, Food Chem., 2005, 90, 3, 417-425, https://doi.org/10.1016/j.foodchem.2004.05.005 . [all data]

Kilic, Hafizoglu, et al., 2004
Kilic, A.; Hafizoglu, H.; Kollmannsberger, H.; Nitz, S., Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L., J. Agric. Food Chem., 2004, 52, 6, 1601-1606, https://doi.org/10.1021/jf0306237 . [all data]

Pino, Marbot, et al., 2003
Pino, J.A.; Marbot, R.; Fuentes, V., Characterization of volatiles in Bullock's heart (Annona reticulata L.) fruit cultivars from Cuba, J. Agric. Food Chem., 2003, 51, 13, 3836-3839, https://doi.org/10.1021/jf020733y . [all data]

Sebastian, Viallon-Fernandez, et al., 2003
Sebastian, I.; Viallon-Fernandez, C.; Berge, P.; Berdague, J.-L., Analysis of the volatile fraction of lamb fat tissue: influence of the type of feeding, Sciences des Aliments, 2003, 23, 4, 497-511, https://doi.org/10.3166/sda.23.497-511 . [all data]

Cadwallader and Heo, 2001
Cadwallader, K.R.; Heo, J., Aroma of roasted sesame oil: characterization by direct thermal desorption-gas chromatography-olfactometry and sample dilution analysis, Am. Chem. Soc. Symp. Ser., 2001, 782, 187-202. [all data]

Kelling, 2001
Kelling, F.J., Olfaction in houseflies: morphology and electrophysiology. Chapter 7. Chemical and electrophysiological analysis of components, present in natural products that attract houseflies, Dissertation, University of Groningen, The Netherlands, 2001. [all data]

Suriyaphan, Drake, et al., 2001
Suriyaphan, O.; Drake, M.; Chen, X.Q.; Cadwallader, K.R., Characteristic aroma components of British farmhouse cheddar cheese, J. Agric. Food Chem., 2001, 49, 3, 1382-1387, https://doi.org/10.1021/jf001121l . [all data]

Czerny and Grosch, 2000
Czerny, M.; Grosch, W., Potent odorants of raw Arabica coffee. Their changes during roasting, J. Agric. Food Chem., 2000, 48, 3, 868-872, https://doi.org/10.1021/jf990609n . [all data]

García, Martín, et al., 2000
García, C.; Martín, A.; Timón, M.L.; Córdoba, J.J., Microbial populations and volatile compounds in the 'bone taint' spoilage of dry cured ham, Lett. Appl. Microbiol., 2000, 30, 1, 61-66, https://doi.org/10.1046/j.1472-765x.2000.00663.x . [all data]

Kotseridis and Baumes, 2000
Kotseridis, Y.; Baumes, R., Identification of impact odorants in Bordeaux red grape juice, in the commercial yeast used for its fermentation, and in the produced wine, J. Agric. Food Chem., 2000, 48, 2, 400-406, https://doi.org/10.1021/jf990565i . [all data]

Novak, Novak, et al., 2000
Novak, J.; Novak, S.; Bitsch, C.; Franz, C.M., Essential oil composition of underground parts of Valeriana celtica ssp. from Austria and Italy, Flavour Fragr. J., 2000, 15, 1, 40-42, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<40::AID-FFJ863>3.0.CO;2-B . [all data]

Tamura, Boonbumrung, et al., 2000
Tamura, H.; Boonbumrung, S.; Yoshizawa, T.; Varanyanond, W., Volatile components of the essential oil in the pulp of four yellow mangoes (Mangifera indica L.) in Thailand, Food Sci. Technol. Res., 2000, 6, 1, 68-73, https://doi.org/10.3136/fstr.6.68 . [all data]

Lopez, Ferreira, et al., 1999
Lopez, R.; Ferreira, V.; Hernandez, P.; Cacho, J.F., Identification of impact odorants of young red wines made with Merlot, Cabernet Sauvignon and Grenache grape varieties: a comparative study, J. Sci. Food Agric., 1999, 79, 11, 1461-1467, https://doi.org/10.1002/(SICI)1097-0010(199908)79:11<1461::AID-JSFA388>3.0.CO;2-K . [all data]

Ong and Acree, 1999
Ong, P.K.C.; Acree, T.E., Similarities in the aroma chemistry of Gewürztraminer variety wines and lychee (Litchi chinesis Sonn.) fruit, J. Agric. Food Chem., 1999, 47, 2, 665-670, https://doi.org/10.1021/jf980452j . [all data]

Schultz, Kaiser, et al., 1999
Schultz, K.; Kaiser, R.; Knudsen, J.T., Cyclanthone and derivatives, new natural products in the flower scent of Cyclanthus bipartitus Poit., Flavour Fragr. J., 1999, 14, 3, 185-190, https://doi.org/10.1002/(SICI)1099-1026(199905/06)14:3<185::AID-FFJ809>3.0.CO;2-7 . [all data]

Doneanu and Anitescu, 1998
Doneanu, C.; Anitescu, G., Supercritical carbon dioxide extraction of Angelica archangelica L. root oil, J. Supercrit. Fluids, 1998, 12, 1, 59-67, https://doi.org/10.1016/S0896-8446(97)00040-5 . [all data]

Fons, Rapior, et al., 1998
Fons, F.; Rapior, S.; Gargadennec, A.; Andary, C.; Bessiere, J.-M., Volatile components of Plantago lanceolata (Plantaginaceae), Acta bot. Gallica, 1998, 145, 4, 265-269, https://doi.org/10.1080/12538078.1998.10516306 . [all data]

Ong and Acree, 1998
Ong, P.K.C.; Acree, T.E., Gas chromatography/olfactory analysis of lychee (Litchi chinesis Sonn.), J. Agric. Food Chem., 1998, 46, 6, 2282-2286, https://doi.org/10.1021/jf9801318 . [all data]

D'Arcy, Rintoul, et al., 1997
D'Arcy, B.R.; Rintoul, G.B.; Rowland, C.Y.; Blackman, A.J., Composition of Australian honey extractives. 1. Norisoprenoids, monoterpenes, and other natural volatiles from blue gum (Eucalyptus leucoxylon) and yellow box (Eucalyptus melliodora) honeys, J. Agric. Food Chem., 1997, 45, 5, 1834-1843, https://doi.org/10.1021/jf960625+ . [all data]

Kondjoyan, Viallon, et al., 1997
Kondjoyan, N.; Viallon, C.; Berdagué, J.L.; Daridan, D.; Simon, M.-N.; Legault, C., Analyse comparative de la fraction volatile de jambons secs de porcs Gascon et Large-White x Landrace Français, J. Rech. C.N.R.S., 1997, 29, 405-410, retrieved from http://www.rennes.inra.fr/srp/jrp/1997/97txtQualite/Q9704.pdf. [all data]

Binder, Benson, et al., 1990
Binder, R.G.; Benson, M.E.; Flath, R.A., Volatile Components of Safflower, J. Agric. Food Chem., 1990, 38, 5, 1245-1248, https://doi.org/10.1021/jf00095a020 . [all data]

Buttery, Takeoka, et al., 1990
Buttery, R.G.; Takeoka, G.; Teranishi, R.; Ling, L.C., Tomato aroma components: identification of glycoside hydrolysis volatiles, J. Agric. Food Chem., 1990, 38, 11, 2050-2053, https://doi.org/10.1021/jf00101a010 . [all data]

Buttery, Teranishi, et al., 1990
Buttery, R.G.; Teranishi, R.; Ling, L.C.; Turnbaugh, J.G., Quantitative and sensory studies on tomato paste volatiles, J. Agric. Food Chem., 1990, 38, 1, 336-340, https://doi.org/10.1021/jf00091a074 . [all data]

Notes

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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