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 Copy

  
• IUPAC Standard InChIKey: PWWAKLGQWQLLIY-UHFFFAOYSA-N Copy
• 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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• Information on this page:
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  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Kovats' RI, non-polar column, custom temperature program

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

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Normal alkane RI, non-polar column, temperature ramp

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

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Tanno, Yokota, et al., 1992
Tanno, N.; Yokota, T.; Abe, M.; Okagami, N., Identification of endogenous gibberellins in dormant bulbils of Chinese yam, Dioscorea opposita, Plant Physiol., 1992, 100, 4, 1823-1826, https://doi.org/10.1104/pp.100.4.1823 . [all data]

Talon M., Koornneef M., et al., 1990
Talon M.; Koornneef M.; Zeevaart J.A.D., Accumulation of C19-gibberelins in the gibbrellin-insensitive dwarf mutant gai if Arabidopsis thaliana (L.) Heynh, Planta, 1990, 182, 4, 501-505, https://doi.org/10.1007/BF02341024 . [all data]

Talon, Koornneef, et al., 1990
Talon, M.; Koornneef, M.; Zeevaart, J.A.D., Endogenous gibberellins in Arabidopsis thaliana and possible steps blocked in the biosynthetic pathways of the semidwarf ga4 and ga5 mutants, Proc. Nat. Acad. Sci. U.S.A., 1990, 87, 20, 7983-7987, https://doi.org/10.1073/pnas.87.20.7983 . [all data]

Talon and Zeevaart, 1990
Talon, M.; Zeevaart, J.A.D., Gibberellins and stem growth as related to photoperiod in Silene armeria L., Plant Physiol., 1990, 92, 4, 1094-1100, https://doi.org/10.1104/pp.92.4.1094 . [all data]

Kim, Lee, et al., 2003
Kim, S.-K.; Lee, S.-C.; Shin, D.-H.; Jang, S.-W.; Nam, J.-W.; Park, T.-S.; Lee, I.-J., Quantification of endogenous gibberellins in leaves and tubers of Chinese yam, Dioscorea opposita Thunb. cv. Tsukune during tuber enlargement, Plant Growth Regul., 2003, 39, 2, 125-130, https://doi.org/10.1023/A:1022569506883 . [all data]

Kappers, Jordi, et al., 1997
Kappers, I.F.; Jordi, W.; Maas, F.M.; van der Plas, L.H.W., Gibberellins in leaves of Alstroemeria hybrida: identification and quantification in relation to leaf age, J. Plant Growth Regul., 1997, 16, 4, 219-225, https://doi.org/10.1007/PL00007000 . [all data]

Kobayashi, Spray, et al., 1996
Kobayashi, M.; Spray, C.R.; Phinney, B.O.; Gaskin, P.; MacMillan, J., Gibberellin metabolism in maize. The stepwise conversion of gibberellin A₁₂-aldehyde to gibberellin A₂₀, Plant Physiol., 1996, 110, 413-418. [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]

Hedden, Hoad, et al., 1993
Hedden, P.; Hoad, G.V.; Gaskin, P.; Lewis, M.J.; Green, J.R.; Furber, M.; Mander, L.N., Kaurenoids and gibberellins, including the newly characterized gibberellin A₈₈, in developing apple seeds, Phytochemistry, 1993, 32, 2, 231-237, https://doi.org/10.1016/S0031-9422(00)94973-2 . [all data]

Gaskin, Gilmour, et al., 1984
Gaskin, P.; Gilmour, S.J.; Lenton, J.R.; MacMillan, J.; Sponsel, V.M., Endogenous gibberellins and kauranoids identified from developing and germinating barley grain, J. Plant Growth Regul., 1984, 2, 1-4, 229-242, https://doi.org/10.1007/BF02042252 . [all data]

Oyama, Yamauchi, et al., 1996
Oyama, N.; Yamauchi, T.; Yamane, H.; Murofushi, N.; Agatsuma, M.; Pour, M.; Mander, L.N., Identification of gibberellins and 9,15-cyclogibberellins in developing apple seeds, Biosci. Biotechnol. Biochem., 1996, 60, 2, 305-308, https://doi.org/10.1271/bbb.60.305 . [all data]

Fujioka, Yamane, et al., 1988
Fujioka, S.; Yamane, H.; Spray, C.R.; Gaskin, P.; Macmillan, J.; Phinney, B.O.; Takahashi, N., Qualitative and quantitative analyses of gibberellins in vegetative shoots of normal, dwarf-1, dwarf-2, dwarf-3, and dwarf-5 seedlings of Zea mays L., Plant Physiol., 1988, 88, 4, 1367-1372, https://doi.org/10.1104/pp.88.4.1367 . [all data]

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

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• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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