GA3, MeTMSi

• Formula: C₂₆H₄₀O₆Si₂
• Molecular weight: 504.7632
• IUPAC Standard InChI: InChI=1S/C26H40O6Si2/c1-16-14-24-15-25(16,32-34(7,8)9)12-10-17(24)26-13-11-18(31-33(4,5)6)23(2,22(28)30-26)20(26)19(24)21(27)29-3/h11,13,17-20H,1,10,12,14-15H2,2-9H3/t17?,18-,19?,20?,23+,24-,25-,26+/m1/s1 Copy

  
• IUPAC Standard InChIKey: QJSHIGDRCGMRDL-RWHUMPPASA-N Copy
• Chemical structure:
  This structure is also available as a 2d Mol file
• Stereoisomers:
  • [14C1]GA3 methyl ester TMS ether
  • iso[14C] GA3 methyl ester TMS ether
  • 3-Epi-GA, MeTMS
  • Iso-GA3, MeTMSi
• Other names: GA3 methyl ester TMS ether; GA3, MeTMS; GA3, methyl ester TMS; Gibberellic acid, MeTMS
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas Chromatography
  • References
  • Notes
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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.

Nakayama, Yokota, et al., 1996
Nakayama, M.; Yokota, T.; Sohma, R.; Mander, L.N.; Twitchin, B.; Komatsu, H.; Matsui, H.; Bukovac, M.J., Gibberellins in immature seed of Prunus cerasus: structure determination and synthesis of gibberellin, GA₉₅ (1,2-didehydro-GA₂₀), Phytochemistry, 1996, 42, 4, 913-920, https://doi.org/10.1016/0031-9422(96)00035-0 . [all data]

Croker, Hedden, et al., 1990
Croker, S.J.; Hedden, P.; Lenton, J.R.; Stoddart, J.L., Comparison of gibberellins in normal and slender barley seedlings, Plant Physiol., 1990, 94, 1, 194-200, https://doi.org/10.1104/pp.94.1.194 . [all data]

Blake, Taylor, et al., 2002
Blake, P.S.; Taylor, J.M.; Finch-Savage, W.E., Identification of abscisic acid, indole-3-acetic acid, jasmonic acid, indole-3-acetonitrile, methyl jasmonate and gibberellins in developing, dormant and startified seeds of ash (Fraxinus excelsior), Plant Growth Regul., 2002, 37, 2, 119-125, https://doi.org/10.1023/A:1020504610172 . [all data]

Gutiérrez-Mañero, Ramos-Solano, et al., 2001
Gutiérrez-Mañero, F.J.; Ramos-Solano, B.; Probanza, A.; Mehouachi, J.; Tadeo, R.; Talon, M., The plant-growth-promoting rhizobacteria Bacillus pumilus and Baillus licheniformis produce high amounts of physiologically active gibberellins, Physiol. Plant., 2001, 111, 2, 206-211, https://doi.org/10.1034/j.1399-3054.2001.1110211.x . [all data]

Taylor, Blake, et al., 2000
Taylor, D.R.; Blake, P.S.; Crisp, C.M., Identification of gibberellins in leaf exudates of strawberry (Fragaria ananassa Duch.), Plant Growth Regul., 2000, 30, 3, 221-223, https://doi.org/10.1023/A:1006385617161 . [all data]

Taylor, Blake, et al., 2000, 2
Taylor, D.R.; Blake, P.S.; Crisp, C.M., Identification of gibberellins in leaf tissues of day-neutral strawberry (Fragaria × ananassa Duch.) cultivars, Plant Growth Regul., 2000, 30, 1, 5-7, https://doi.org/10.1023/A:1006275024517 . [all data]

Davis, Kobayashi, et al., 1999
Davis, G.; Kobayashi, M.; Phinney, B.O.; Lange, T.; Croker, S.J.; Gaskin, P.; MacMillan, J., Gibberellin biosynthesis in maize. Metabolic studies with GA₁₅, GA₂₄, GA₂₅, GA₇, and 2,3-dehydro-GA₉, Plant Physiol., 1999, 121, 3, 1037-1045, https://doi.org/10.1104/pp.121.3.1037 . [all data]

Roberts, Blake, et al., 1999
Roberts, A.V.; Blake, P.S.; Lewis, R.; Taylor, J.M.; Dunstan, D.I., The effect of gibberellins on flowering in roses, J. Plant Growth Regul., 1999, 18, 3, 113-119, https://doi.org/10.1007/PL00007058 . [all data]

Webb, Appleford, et al., 1998
Webb, S.E.; Appleford, N.E.J.; Gaskin, P.; Lenton, J.R., Gibberellins in internodes and ears of wheat containing different dwarfing alleles, Phytochemistry, 1998, 47, 5, 671-677, https://doi.org/10.1016/S0031-9422(97)00684-5 . [all data]

Grünzweig, Rabinowitch, et al., 1997
Grünzweig, J.M.; Rabinowitch, H.D.; Katan, J.; Wodner, M.; Ben-Tal, Y., Endogenous gibberellins in foliage of tomato (Lycopersicon esculentum), Phytochemistry, 1997, 46, 5, 811-815, https://doi.org/10.1016/S0031-9422(97)00383-X . [all data]

MacMillan and Gaskin, 1996
MacMillan, J.; Gaskin, P., Gibberellins in endosperm and embryos of Marah macrocarpus, Phytochemistry, 1996, 42, 5, 1263-1266, https://doi.org/10.1016/0031-9422(96)00179-3 . [all data]

Spray, Kobayashi, et al., 1996
Spray, C.R.; Kobayashi, M.; Suzuki, Y.; Phinney, B.O.; Gaskin, P.; MacMillan, J., The dwarf-1 (dl) mutant of Zea mays blocks three steps in the gibberellin-biosynthetic pathway, Proc. Nat. Acad. Sci. U.S.A., 1996, 93, 19, 10515-10518, https://doi.org/10.1073/pnas.93.19.10515 . [all data]

Santes, Hedden, et al., 1995
Santes, C.M.; Hedden, P.; Gaskin, P.; Garcia-Martinez, J.L., Gibberellins and related compounds in young fruits of pea and their relationship to fruit-set, Phytochemistry, 1995, 40, 5, 1347-1355, https://doi.org/10.1016/0031-9422(95)00489-T . [all data]

Blake and Browning, 1994
Blake, P.S.; Browning, G., Gibberellins in developing fruits of Prunus avium, Phytochemistry, 1994, 35, 6, 1383-1386, https://doi.org/10.1016/S0031-9422(00)86860-0 . [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]

Waycott, Smith, et al., 1991
Waycott, W.; Smith, V.A.; Gaskin, P.; MacMillan, J.; Taiz, L., The endogenous gibberellins of dwarf mutants of lettuce, Plant Physiol., 1991, 95, 4, 1169-1173, https://doi.org/10.1104/pp.95.4.1169 . [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]

Koshioka, Pharis, et al., 1988
Koshioka, M.; Pharis, R.P.; Matsuta, N.; Mander, L.N., Metabolism of [3H]gibberellin A5 and [2H]gibberellin A5 in cell suspension cultures of prunus persica, Phytochemistry, 1988, 27, 12, 3799-3805, https://doi.org/10.1016/0031-9422(88)83020-6 . [all data]

Chung, Kuo, et al., 2003
Chung, J.-D.; Kuo, S.-R.; Chien, C.-T., Identification and quantification of gibberellin transformation and dosage changes in good and poor flowering clones of Calocedrus formosana grafts, Taiwan J. For. Sci., 2003, 18, 4, 387-400. [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]

Nakayama, Koshioka, et al., 2001
Nakayama, M.; Koshioka, M.; Matsui, H.; Ohara, H.; Mander, L.N.; Leitch, S.K.; Twitchin, B.; Kraft-Klaunzer, P.; Pharis, R.P.; Yokota, T., Endogenous gibberellins in immature seeds of Prunus persica L.: identification of GA₁₁₈, GA₁₁₉, GA₁₂₀, GA₁₂₁, GA₁₂₂ and GA₁₂₆, Phytochemistry, 2001, 57, 5, 749-758, https://doi.org/10.1016/S0031-9422(01)00154-6 . [all data]

Fos, Nuez, et al., 2000
Fos, M.; Nuez, F.; Garcia-Martinez, J.L., The gene pat-2, which induces natural partenocarpy, alters the gibberellin content in unpollinated tomato ovaries, Plant Physiol., 2000, 122, 2, 471-479, https://doi.org/10.1104/pp.122.2.471 . [all data]

Pérez, Viani, et al., 2000
Pérez, F.J.; Viani, C.; Retamales, J., Bioactive gibberellins in seeded and seedless grapes: identification and changes in content during berry development, Am. J. Enol. Vitic, 2000, 51, 4, 315-318. [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]

Garcia-Martinez, Santes, et al., 1991
Garcia-Martinez, J.L.; Santes, C.; Croker, S.J.; Hedden, P., Identification, quantitation and distribution of gibberellins in fruits of Pisum sativum L. cv. Alaska during pod development, Planta, 1991, 184, 1, 53-60, https://doi.org/10.1007/BF00208236 . [all data]

Matheussen, Morgan, et al., 1991
Matheussen, A.-M.; Morgan, P.W.; Frederiksen, R.A., Implication of gibberellins in head smut (Sporisorium reilianum) of Sorghum bicolor, Plant Physiol., 1991, 96, 2, 537-544, https://doi.org/10.1104/pp.96.2.537 . [all data]

Notes

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