4aα,4bβ-Gibbane-1α,10β-dicarboxylic acid, 1,4a-dimethyl-8-methylene-, dimethyl ester

Formula: C₂₂H₃₂O₄
Molecular weight: 360.4871
IUPAC Standard InChI: InChI=1S/C22H32O4/c1-13-11-22-12-14(13)7-8-15(22)20(2)9-6-10-21(3,19(24)26-5)17(20)16(22)18(23)25-4/h14-17H,1,6-12H2,2-5H3
IUPAC Standard InChIKey: PWWAKLGQWQLLIY-UHFFFAOYSA-N
CAS Registry Number: 22882-62-8
Chemical structure:
This structure is also available as a 2d Mol file
Other names: Dimethyl 1,4a-dimethyl-8-methylenegibbane-1,10-dicarboxylate, (1α,4aα,4bβ,10β)-; GA12, Me; GA12 methyl ester; GA12, Me-TMS; GA12, Methylated; Trachylo-GA12, methyl ester
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Other data available:
- Mass spectrum (electron ionization)
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Normal alkane RI, non-polar column, custom temperature program

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	5 % Phenyl methyl siloxane	DB-1	BPX-5	BPX-5	SE-30
Column length (m)		30.			25.
Carrier gas		He
Substrate
Column diameter (mm)		0.25			0.25
Phase thickness (μm)		0.25			0.25
Program	not specified	60C92min) => 30C/min => 210C => 2C/min => 280C(5min)		60 0C (1.5 min) 25 K/min -> 150 0C 2 K/min -> 230 0C 70 K/min -> 300 0C	60 (2min) => 20C/min => 200C => 4C/min => 260C
I	2360.	2359.	2324.	2324.	2359.
Reference	Davidson, Elliott, et al., 2003	Yamazaki, Nishijima, et al., 2002	Helliwell, Chandler, et al., 2001	Helliwell, Chandler, et al., 2001	Wang, Little, et al., 1996
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SE-30	DB-1	Polydimethyl siloxane	Polydimethyl siloxane	DB-1
Column length (m)	25.	15.			25.
Carrier gas		He			He
Substrate
Column diameter (mm)	0.25	0.25			0.32
Phase thickness (μm)	0.25				0.33
Program	60 (2min) => 20C/min => 200C => 4C/min => 260C	80C(1min) => 30C/min => 245C => 5C/min => 300C	not specified	not specified	50C(1min) => 20C/min => 240C => 4C/min => 295C
I	2361.	2371.	2344.	2348.	2369.
Reference	Wang, Little, et al., 1996	Kawaide, Sassa, et al., 1995	Tanno, Nakayama, et al., 1995	Tanno, Nakayama, et al., 1995	Lange, Hedden, et al., 1993
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	Ultra-2
Column length (m)	25.
Carrier gas
Substrate
Column diameter (mm)	0.32
Phase thickness (μm)	0.52
Program	50C => 40C/min => 220C => 8C/min => 280C
I	2331.
Reference	Talon, Zeevaart, et al., 1991
Comment	MSDC-RI

References

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

Davidson, Elliott, et al., 2003
Davidson, S.E.; Elliott, R.C.; Helliwell, C.A.; Poole, A.T.; Reid, J.B., The PEa gene NA encodes ent-Kaurenoic acid oxidase, Plant Physiol., 2003, 131, 1, 335-344, https://doi.org/10.1104/pp.012963 . [all data]

Yamazaki, Nishijima, et al., 2002
Yamazaki, H.; Nishijima, T.; Koshioka, M.; Miura, H., Gibberellins do no act against abscisic acid in the regulation of bulb dormancy of Allium wakegi Araki, Plant Growth Regul., 2002, 36, 3, 223-229, https://doi.org/10.1023/A:1016577529378 . [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]

Wang, Little, et al., 1996
Wang, Q.; Little, C.H.A.; Moritz, T.; Odén, P.C., Identification of endogenous gibberellins, and metabolism of tritiated and deuterated GA₄, GA₉, and GA₂₀, in Scots pine (Pinus sylvestris) shoots, Physiol. Plant., 1996, 97, 4, 764-771, https://doi.org/10.1111/j.1399-3054.1996.tb00542.x . [all data]

Kawaide, Sassa, et al., 1995
Kawaide, H.; Sassa, T.; Kamiya, Y., Plant-like biosynthesis of gibberellin A₁ in the fungus Phaeosphaeria Sp. L487, Phytochemistry, 1995, 39, 2, 305-310, https://doi.org/10.1016/0031-9422(95)00006-S . [all data]

Tanno, Nakayama, et al., 1995
Tanno, N.; Nakayama, M.; Kurosawa, H.; Wakatsuki, M.; Tanno, M.; Abe, M.; Okagami, N.; Yokota, T., Endogenous gibberellins from three East Asian Stenophora species of the genus Dioscorea (Yams), Z. Naturforsch., 1995, 50c, 193-198. [all data]

Lange, Hedden, et al., 1993
Lange, T.; Hedden, P.; Graebe, J.E., Biosynthesis of 12α- and 13-hydroxylated gibberellins in a cell-free system from Cucurbita maxima endosperm and the identification of new endogenous gibberellins, Planta, 1993, 189, 3, 340-349, https://doi.org/10.1007/BF00194430 . [all data]

Talon, Zeevaart, et al., 1991
Talon, M.; Zeevaart, J.A.D.; Gage, D.A., Identification of gibberellins in spinach and effects of light and darkness on their levels, Plant Physiol., 1991, 97, 4, 1521-1526, https://doi.org/10.1104/pp.97.4.1521 . [all data]

Notes

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

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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