Kaur-16-en-18-oic acid, methyl ester, (4β)-

Formula: C₂₁H₃₂O₂
Molecular weight: 316.4776
IUPAC Standard InChI: InChI=1S/C21H32O2/c1-14-12-21-11-8-16-19(2,17(21)7-6-15(14)13-21)9-5-10-20(16,3)18(22)23-4/h15-17H,1,5-13H2,2-4H3
IUPAC Standard InChIKey: DWTRNJFPDXIFSY-UHFFFAOYSA-N
CAS Registry Number: 5524-25-4
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
Other names: Kaur-16-en-19-oic acid, methyl ester; Argyrophilic acid methyl ester; Methyl kaur-16-en-18-oate, ((4β)-; (4aR,6aR,9R,11aS,11bR)-Methyl 4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate; ent-Kaurenoic acid methyl ester; ent-Kaurenoic acid, Me; Kaur-16-en-18-oic acid, methyl ester
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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, custom temperature program

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	2313.7	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)
Capillary	HP-1	2285.	Helliwell, Poole, et al., 1999	25. m/0.22 mm/0.33 μm; Program: 60C(1.5min) => 25C/min => 200C => 5C/min => 300C
Capillary	HP-1	2286.	Helliwell, Poole, et al., 1999	25. m/0.22 mm/0.33 μm; Program: 60C(1.5min) => 25C/min => 200C => 5C/min => 300C
Capillary	BPX-5	2242.	Helliwell, Poole, et al., 1999	25. m/0.22 mm/0.25 μm; Program: 60C(1.5min) => 25C/min => 200C => 5C/min => 300C
Capillary	BPX-5	2242.	Helliwell, Poole, et al., 1999	25. m/0.22 mm/0.25 μm; Program: 60C(1.5min) => 25C/min => 200C => 5C/min => 300C
Capillary	DB-1	2270.	Pearce, Koshioka, et al., 1994	15. m/0.22 mm/0.25 μm; Program: 60(0.1 min)-200 0C at 20 deg/min; 200-300 0C at 5 deg/min

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	BPX-5	2292.	Helliwell, Chandler, et al., 2001
Capillary	BPX-5	2291.	Helliwell, Chandler, et al., 2001	Program: 60 0C (1.5 min) 25 K/min -> 150 0C 2 K/min -> 230 0C 70 K/min -> 300 0C

References

Go To: Top, Gas Chromatography, Notes

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Helliwell, Poole, et al., 1999
Helliwell, C.A.; Poole, A.; Peacock, W.J.; Dennis, E.S., Arabidopsis ent-Kaurene Oxidase Catalyzes Three Steps of Gibberellin Biosynthesis, Plant Physiol., 1999, 119, 2, 507-510, https://doi.org/10.1104/pp.119.2.507 . [all data]

Pearce, Koshioka, et al., 1994
Pearce, D.W.; Koshioka, M.; Pharis, R.P., Chromatography of gibberellins, J. Chromatogr. A, 1994, 658, 1, 91-122, https://doi.org/10.1016/0021-9673(94)85210-3 . [all data]

Helliwell, Chandler, et al., 2001
Helliwell, C.A.; Chandler, P.M.; Poole, A.; Dennis, E.S.; Peacock, W.J., The CYP88A cytochrome P450, ent-kaurenoic acid oxidase, catalyzes three steps of the gibberellin biosynthesis pathway, Proc. Natl. Acad. Sci. U.S.A, 2001, 98, 4, 2065-2070, https://doi.org/10.1073/pnas.98.4.2065 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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