1,2,3-Propanetricarboxylic acid, 2-[(trimethylsilyl)oxy]-, tris(trimethylsilyl) ester

Formula: C₁₈H₄₀O₇Si₄
Molecular weight: 480.8480
IUPAC Standard InChI: InChI=1S/C18H40O7Si4/c1-26(2,3)22-15(19)13-18(25-29(10,11)12,17(21)24-28(7,8)9)14-16(20)23-27(4,5)6/h13-14H2,1-12H3
IUPAC Standard InChIKey: VFGAVMGYDWDESE-UHFFFAOYSA-N
CAS Registry Number: 14330-97-3
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: Citric acid, tetrakis(trimethylsilyl) deriv.; Tris(trimethylsilyl) 2-[(trimethylsilyl)oxy]-1,2,3-propanetricarboxylate; Citric acid, tetrakis-TMS; Citric acid, tetra-TMS; Citric acid, TMS; Citric acid, 4TMS derivative; Citric acid, trimethylsilyl ether, tris(trimethylsilyl) ester; Citric acid, (4TMS); Propane-1,2,3-tricarboxylic acid, 2-trimethylsilyloxy, tris-trimethylsilyl ester; 1,2,3-Propanetricarboxylic acid, 2-[(trimethylsilyl)oxy]-, tris(trimethylsilyl)
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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

Kovats' RI, non-polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	OV-1	160.	1847.	Petersson, 1977	N2, Chromosorb G (100-120 mesh); Column length: 2. m

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5MS	1815.7	Jonsson, Johansson, et al., 2005	10. m/0.18 mm/0.18 μm, 70. C @ 2. min, 40. K/min, 320. C @ 2. min
Capillary	DB-5	1838.	Kimura, Yamamoto, et al., 1999	30. m/0.25 mm/1. μm, He, 100. C @ 4. min, 4. K/min, 290. C @ 10. min
Capillary	DB-1	1839.	Hoffmann, Aramaki, et al., 1989	30. m/0.53 mm/1. μm, He, 4. K/min; T_start: 70. C; T_end: 290. C
Capillary	OV-1	1853.	Lefevere, Verhaeghe, et al., 1989	10. m/0.22 mm/0.17 μm, He, 5. K/min; T_start: 70. C; T_end: 270. C
Capillary	SE-52	1845.	Lefevere, Verhaeghe, et al., 1989	25. m/0.32 mm/0.52 μm, He, 5. K/min; T_start: 70. C; T_end: 270. C
Capillary	CP Sil 5 CB	1839.	Wurth, Kumps, et al., 1989	N2, 60. C @ 0.5 min, 6. K/min, 280. C @ 5. min
Capillary	SE-52	1846.	Lefevere, Verhaeghe, et al., 1988	25. m/0.20 mm/0.40 μm, He, 5. K/min; T_start: 50. C; T_end: 270. C
Capillary	Ultra-2	1853.	Tuchman, Bowers, et al., 1984	25. m/0.31 mm/0.52 μm, He, 5. K/min; T_start: 50. C; T_end: 300. C
Packed	OV-1	1841.	Tanaka, Hine, et al., 1980	N2, 100-120 mesh, 70. C @ 0.5 min, 28. K/min; Column length: 1.8 m; T_end: 290. C
Packed	OV-1	1857.	Butts, 1972	He, Chromosorb W HP (80-100 mesh), 10. K/min; Column length: 2. m; T_start: 100. C; T_end: 325. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	Polydimethyl siloxane with 5 % phenyl groups	1800.	Kempa, Hummel, et al., 2009	Program: not specified
Capillary	VF-5MS	1800.	Tret'yakov, 2007	30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C
Capillary	DB-1	1835.	Tsai, Oliphant, et al., 1985	He; Program: not specified
Packed	OV-101	1841.	Tanaka and Hine, 1982	Program: not specified

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5 MS	1834.	Yan, A., et al., 2009	10. m/0.18 mm/0.18 μm, Helium, 70. C @ 2. min, 35. K/min, 310. C @ 2. min
Capillary	HP-5MS	1863.	Lee, Yanamandra, et al., 2002	30. m/0.25 mm/0.25 μm, He, 70. C @ 3. min, 4. K/min, 280. C @ 3. min

References

Go To: Top, Gas Chromatography, Notes

Petersson, 1977
Petersson, G., Retention Data in GLC Analysis; Carbohydrate-Related Hydroxy Carboxylic and Dicarboxylic Acids as Trimethylsilyl Derivatives, J. Chromatogr. Sci., 1977, 15, 7, 245-255, https://doi.org/10.1093/chromsci/15.7.245 . [all data]

Jonsson, Johansson, et al., 2005
Jonsson, P.; Johansson, A.I.; Gullberg, J.; Trygg, J.; Jiye, A.; Grung, B.; Marklund, S.; Sjöström, M.; Antti, H.; Moritz, T., High-throughput data analysis for detecting and identifying differences between samples in GC/MS-based metabolomic analyses, Anal. Chem., 2005, 77, 17, 5635-5642, https://doi.org/10.1021/ac050601e . [all data]

Kimura, Yamamoto, et al., 1999
Kimura, M.; Yamamoto, T.; Yamaguchi, S., Automated metabolic profiling and interpretation of GC/MS data for organic acidemia screening: a personal computer-based system, Tohoku J. Exp. Med., 1999, 188, 4, 317-334, https://doi.org/10.1620/tjem.188.317 . [all data]

Hoffmann, Aramaki, et al., 1989
Hoffmann, G.; Aramaki, S.; Blum-Hoffmann, E.; Nyhan, W.L.; Sweetman, L., Quantitative analysis for organic acids in biological samples: batch isolation followed by gas chromatographic-mass spectrometric analysis, Clin. Chem., 1989, 35, 4, 587-595. [all data]

Lefevere, Verhaeghe, et al., 1989
Lefevere, M.F.; Verhaeghe, B.J.; Declerck, D.H.; Van Bocxlaer, J.F.; De Leenheer, A.P.; De Sagher, R.M., Metabolic Profiling of Urinary Organic Acids by Single and Multicolumn Capillary Gas Chromatography, J. Chromatogr. Sci., 1989, 27, 1, 23-29, https://doi.org/10.1093/chromsci/27.1.23 . [all data]

Wurth, Kumps, et al., 1989
Wurth, C.; Kumps, A.; Mardens, Y., Urinary organic acids: Retention indices on two capillary gas chromatography columns, J. Chromatogr., 1989, 491, 186-192, https://doi.org/10.1016/S0378-4347(00)82831-5 . [all data]

Lefevere, Verhaeghe, et al., 1988
Lefevere, M.F.; Verhaeghe, B.J.; Declerck, D.M.; de Leenheer, A.P., Automated profiling of urinary organic acids by dual-column gas chromatography and gas chromatography/mass spectrometry, Biomed. Environ. Mass Spectrom., 1988, 15, 6, 311-322, https://doi.org/10.1002/bms.1200150603 . [all data]

Tuchman, Bowers, et al., 1984
Tuchman, M.; Bowers, L.D.; Fregien, K.D.; Crippin, P.J.; Krivit, W., Capillary Gas Chromatographic Separation of Urinary Organic Acids. Retention Indices of 101 Urinary Acids on a 5% Phenylmethyl Silicone Capillary Column, J. Chromatogr. Sci., 1984, 22, 5, 198-202, https://doi.org/10.1093/chromsci/22.5.198 . [all data]

Tanaka, Hine, et al., 1980
Tanaka, K.; Hine, D.G.; West-Dull, A.; Lynn, T.B., Gas-chromatographic method of analysis for urinary organic acids. I. Retention indices of 155 metabolically important compounds, Clin. Chem., 1980, 26, 13, 1839-1846. [all data]

Butts, 1972
Butts, W.C., Two-Column Gas Chromatography of Trimethylsilyl Derivatives of Biochemically Significant Compounds, Anal. Biochemistry, 1972, 46, 1, 187-199, https://doi.org/10.1016/0003-2697(72)90411-3 . [all data]

Kempa, Hummel, et al., 2009
Kempa, S.; Hummel, J.; Schwemmer, T.; Pietzke, M.; Strehmel, N.; Wienkoop, S.; Kopka, J.; Weckwerth, W., An automated GCxGC-TOF-MS protocol for batch-wise extraction and alinmebt of mass isotopomer matrixes from differential 13C-labeling experiments: a case study for photoautotrophic-mixotrophic grown Chlamydomonas reinhardtii cells, J. Basic Microbiol., 2009, 49, 1, 82-91, https://doi.org/10.1002/jobm.200800337 . [all data]

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

Tsai, Oliphant, et al., 1985
Tsai, M.Y.; Oliphant, C.; Josephson, M.W., Identification of Metabolites Diagnostic for Organic Acidurias by Simultaneous Dual-Column Capillary Gas Chromatography, J. Chromatogr., 1985, 341, 1-10, https://doi.org/10.1016/S0378-4347(00)84004-9 . [all data]

Tanaka and Hine, 1982
Tanaka, K.; Hine, D.G., Compilation of Gas Chromatographic Retention Indices of 163 Metabolically Important Organic Acids, and Their Use in Detection of Patients with Organic Acidurias, J. Chromatogr., 1982, 239, 301-322, https://doi.org/10.1016/S0021-9673(00)81990-1 . [all data]

Yan, A., et al., 2009
Yan, B.; A.; Wang, G.; Lu, H.; Huang, X.; Liu, Y.; Zha, W.; Hao, H.; Zhang, Y.; Liu, L.; Gu, S.; Huang, Q.; Zheng, Y.; Sun, J., Metabolomic investigation into variation of endogenous metabolites in professional athletes subject to strength-endurance training, J. Appl. Physiol., 2009, 106, 2, 531-538, https://doi.org/10.1152/japplphysiol.90816.2008 . [all data]

Lee, Yanamandra, et al., 2002
Lee, B.Y.; Yanamandra, K.; Thurmon, T.F., Quantitative estimation of organic analytes with a capillary column, Am. Clin. Lab., 2002, May, 30-34. [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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