Brassinolide

Brassinolide is a plant hormone. The first isolated brassinosteroid, it was discovered when it was shown that pollen from rapeseed (Brassica napus) could promote stem elongation and cell division.[1] The biologically active component was isolated and named brassinolide.[2]

Brassinolide
Names
IUPAC name
(22R,23R)-2α,3α,22,23-Tetrahydroxy-6,7-seco-5α-campestano-6,7-lactone
Systematic IUPAC name
(1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-1-[(2S,3R,4R,5S)-3,4-Dihydroxy-5,6-dimethylheptan-2-yl]-8,9-dihydroxy-10a,12a-dimethylhexadecahydro-6H-indeno[4,5-d][2]benzoxepin-6-one
Other names
2,3,22,23-Tetrahydroxy-β-homo-7-oxaergostan-6-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C28H48O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14-25,29-32H,7-13H2,1-6H3/t15-,16-,17-,18+,19-,20-,21+,22-,23+,24+,25+,27+,28+/m0/s1 checkY
    Key: IXVMHGVQKLDRKH-KNBKMWSGSA-N checkY
  • InChI=1/C28H48O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14-25,29-32H,7-13H2,1-6H3/t15-,16-,17-,18+,19-,20-,21+,22-,23+,24+,25+,27+,28+/m0/s1
    Key: IXVMHGVQKLDRKH-KNBKMWSGBW
  • O=C3OC[C@H]2[C@@H]1CC[C@@H]([C@@]1(C)CC[C@@H]2[C@@]4(C)C[C@@H](O)[C@@H](O)C[C@H]34)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C
Properties
C28H48O6
Molar mass 480.686 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

References
  1. Mitchell JW, Mandava N, Worley JF, Plimmer JR, Smith MV (1970). "Brassins--a new family of plant hormones from rape pollen". Nature. 225 (5237): 1065–6. Bibcode:1970Natur.225.1065M. doi:10.1038/2251065a0. PMID 16056912. S2CID 4116426.
  2. Grove, Michael D.; Spencer, Gayland F.; Rohwedder, William K.; Mandava, Nagabhushanam; Worley, Joseph F.; Warthen, J. David; Steffens, George L.; Flippen-Anderson, Judith L.; Cook, J. Carter (1979). "Brassinolide, a plant growth-promoting steroid isolated from Brassica napus pollen". Nature. 281 (5728): 216–217. Bibcode:1979Natur.281..216G. doi:10.1038/281216a0. S2CID 4335601.
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