Butanoic acid, 3-hydroxy-, methyl ester

Formula: C₅H₁₀O₃
Molecular weight: 118.1311
IUPAC Standard InChI: InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3
IUPAC Standard InChIKey: LDLDJEAVRNAEBW-UHFFFAOYSA-N
CAS Registry Number: 1487-49-6
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.
Stereoisomers:
- Butanoic acid, 3-hydroxy-, methyl ester, (S)-
Other names: Butyric acid, 3-hydroxy-, methyl ester; Methyl 3-hydroxybutanoate; Methyl β-hydroxybutyrate; Methyl 3-hydroxybutyrate; CH3CH(OH)CH2C(O)OCH3; β-Hydroxybutyric acid, methyl ester; (.+/-.)-3-Hydroxybuytyric acid, methyl ester
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Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	DB-1	864.	Osorio, Alarcon, et al., 2006	25. m/0.2 mm/0.33 μm, 4. K/min; T_start: 50. C; T_end: 300. C
Capillary	HP-5MS	858.	Pino, Mesa, et al., 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	CP Sil 5 CB	820.	Pino, Almora, et al., 2003	60. m/0.32 mm/0.25 μm, He, 60. C @ 10. min, 3. K/min, 280. C @ 60. min
Capillary	HP-5MS	859.	Kim T.H., Kim T.H., et al., 2002	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 3. K/min, 200. C @ 20. min

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	VF-5MS	882.5	Tret'yakov, 2007	30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Innowax	1475.	Lee, Lee, et al., 2006	60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 230. C @ 20. min
Capillary	DB-Wax	1461.	Osorio, Alarcon, et al., 2006	30. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 4. K/min, 220. C @ 20. min
Capillary	AT-Wax	1465.	Pino, Almora, et al., 2003	60. m/0.32 mm/0.25 μm, He, 65. C @ 10. min, 2. K/min, 250. C @ 60. min
Capillary	DB-Wax	1478.	Kim T.H., Kim T.H., et al., 2002	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 3. K/min, 200. C @ 20. min
Capillary	DB-Wax	1475.	Umano, Hagi, et al., 1992	He, 40. C @ 10. min, 2. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_end: 200. C
Capillary	DB-Wax	1460.	Suárez, Duque, et al., 1991	30. m/0.259 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C
Capillary	DB-Wax	1460.	Suárez, Duque, et al., 1991	30. m/0.259 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C
Capillary	DB-Wax	1459.	Suárez, Duque, et al., 1991	30. m/0.259 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C
Capillary	DB-Wax	1460.	Suárez, Duque, et al., 1991	30. m/0.259 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-1	826.	Teai, Claude-Lafontaine, et al., 2001	50. m/0.32 mm/0.52 μm, N2; Program: 40C => 2C/min => 130C => 4C/min => 250C

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1454.	Weckerle, Bastl-Borrmann, et al., 2001	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 220. C
Capillary	DB-Wax	1466.	Takeoka and Butter, 1989	60. m/0.32 mm/0.25 μm, He, 30. C @ 4. min, 2. K/min; T_end: 180. C
Capillary	DB-Wax	1467.	Takeoka and Butter, 1989	60. m/0.32 mm/0.25 μm, He, 30. C @ 4. min, 2. K/min; T_end: 180. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1445.	Parker, Tsormpatsidis, et al., 2010	Program: not specified
Capillary	Supelko CO Wax	1484.	Vekiari, Orepoulou, et al., 2010	60. m/0.32 mm/0.25 μm, Helium; Program: 40 0C (5 min) 4 0C/min -> 75 0C 5 0C/min -> 250 0C (10 min)
Capillary	Carbowax 20M	1454.	Vinogradov, 2004	Program: not specified
Capillary	DB-Wax	1460.	Mayorga, Knapp, et al., 2001	30. m/0.25 mm/0.25 μm; Program: 50C(4min) => 4C/min => 130C => 1C/min => 190C => 4C/min => 220C(20min)
Capillary	DB-Wax	1468.	Mayorga, Knapp, et al., 2001	30. m/0.25 mm/0.25 μm; Program: 50C(4min) => 4C/min => 130C => 1C/min => 190C => 4C/min => 220C(20min)
Capillary	Carbowax 20M	1475.	Teai, Claude-Lafontaine, et al., 2001	50. m/0.2 mm/0.2 μm, N2; Program: 60C => 2C/min => 150C => 4C/min => 220C
Capillary	Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.	1460.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Osorio, Alarcon, et al., 2006
Osorio, C.; Alarcon, M.; Moreno, C.; Bonilla, A.; Barrios, J.; Garzon, C.; Duque, C., Characterization of Odor-Active Volatiles in Champa ( Campomanesia lineatifolia R. P.), J. Agric. Food Chem., 2006, 54, 2, 509-516, https://doi.org/10.1021/jf052098c . [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

Pino, Almora, et al., 2003
Pino, J.; Almora, K.; Marbot, R., Volatile components of papaya (Carica papaya L., maradol variety) fruit, Flavour Fragr. J., 2003, 18, 6, 492-496, https://doi.org/10.1002/ffj.1248 . [all data]

Kim T.H., Kim T.H., et al., 2002
Kim T.H.; Kim T.H.; Shin J.H.; Yu E.J.; Kim Y.S.; Lee H.J., Characteristics of aroma-active compounds in the pectin-elicited suspension culture of Zanthoxylum piperitum (prickly ash), Biotechnology Letters, 2002, 24, 7, 551-556, https://doi.org/10.1023/A:1014812508441 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Lee, Lee, et al., 2006
Lee, S.-J.; Lee, J.-E.; Kim, H.-W.; Kim, S.-S.; Koh, K.-H., Development of Korean red wines using Vitis labrusca varieties: instrumental and sensory characterization, Food Chem., 2006, 94, 3, 385-393, https://doi.org/10.1016/j.foodchem.2004.11.035 . [all data]

Umano, Hagi, et al., 1992
Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T., Volatile constituents of green and ripened pineapple (Aanas comosus [L.] Merr.), J. Agric. Food Chem., 1992, 40, 4, 599-603, https://doi.org/10.1021/jf00016a014 . [all data]

Suárez, Duque, et al., 1991
Suárez, M.; Duque, C.; Wintoch, H.; Schreier, P., Glycosidically bound aroma compounds from the pulp and the peelings of lulo fruit (Solanum vestissimum D.), J. Agric. Food Chem., 1991, 39, 9, 1643-1645, https://doi.org/10.1021/jf00009a022 . [all data]

Teai, Claude-Lafontaine, et al., 2001
Teai, T.; Claude-Lafontaine, A.; Schippa, C.; Cozzolino, F., Volatile compounds in fresh pulp of pineapple (Ananas comosus [L.] Merr.) from French Polynesia, J. Essent. Oil Res., 2001, 13, 5, 314-318, https://doi.org/10.1080/10412905.2001.9712222 . [all data]

Weckerle, Bastl-Borrmann, et al., 2001
Weckerle, B.; Bastl-Borrmann, R.; Richling, E.; Hör, K.; Ruff, C.; Schreier, P., Cactus pear (Opuntia ficus indica) flavour constituents - chiral evaluation (MDGC-MS) and isotope ratio (HRGC-IRMS) analysis, Flavour Fragr. J., 2001, 16, 5, 360-363, https://doi.org/10.1002/ffj.1012 . [all data]

Takeoka and Butter, 1989
Takeoka, G.; Butter, R.G., Volatile constituents of pineapple (Ananas Comosus [L.] Merr.) in Flavor Chemistry. Trends and Developments, Teranishi,R.; Buttery,R.G.; Shahidi,F., ed(s)., American Chemical Society, Washington, DC, 1989, 223-237. [all data]

Parker, Tsormpatsidis, et al., 2010
Parker, J.K.; Tsormpatsidis, E.; Elmore, J.S.; Wagstaffe, A.; Mottram, D.S., Solid-phase extraction as a routine method for comparing key aroma compounds in fruits in Expression of Multidisciplinary Flavour Science, Blank, I.; Wust, M.; Yeretzian C., ed(s)., Zurcher Hochschule fur Angewandte Wissenschaften, Wadenswil, Switzerland, 2010, 521-524. [all data]

Vekiari, Orepoulou, et al., 2010
Vekiari, S.A.; Orepoulou, V.; Kourkoutas, Y.; Kamoun, N.; Msallem, M.; Psimouli, V.; Arapoglou, D., Characterization and seasonal variations of the quality of virgin olive oil of the Thoumbolia and Koroneiki varieties from Southern Greece, Grasas y Aceites, 2010, 61, 3, 221-231, https://doi.org/10.3989/gya.108709 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Mayorga, Knapp, et al., 2001
Mayorga, H.; Knapp, H.; Winterhalter, P.; Duque, C., Glycosidically bound flavor compounds of cape gooseberry (Physalis peruviana L.), J. Agric. Food Chem., 2001, 49, 4, 1904-1908, https://doi.org/10.1021/jf0011743 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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