Isohomobrassinolide

Names

[ Name ]:
Isohomobrassinolide

[Synonym ]:
Cholest-5-ene-3|A,22-diol
22R-hydroxycholesterol
(22R)-22-hydroxycholesterol
cholest-5-en-3beta,22-diol
22S,23S-28-homobrassinolide
22S,23S-homobrassinolide
22(S)-hydroxycholesterol
3H-Benz[c]indeno[5,4-e]oxepin-3-one, 10-[(1S,2S,3S,4S)-4-ethyl-2,3-dihydroxy-1,5-dimethylhexyl]hexadecahydro-5,6-dihydroxy-7a,9a-dimethyl-, (3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-
Cholest-5-ene-3beta,22-diol
(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(2S,3S,4S,5S)-5-Ethyl-3,4-dihydroxy-6-methyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
22-Hydroxycholesterol
(22S)-22-Hydroxycholesterol
Isohomobrassinolide

Biological Activity

[Description]:

(22S,23S)-Homobrassinolide is one of the most active brassinosteroids in inducing plant growth in various plant bioassay systems. (22S,23S)-Homobrassinolide shows Akt-dependent anabolic activity in rat skeletal muscle cells. Orally active[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[In Vitro]

(22S,23S)-Homobrassinolide slightly stimulates ferricyanide reduction and promotes uptake of sucrose and alpha-aminoisobutyric acid [2].

[References]

[1]. Esposito D, et al. Akt-dependent anabolic activity of natural and synthetic brassinosteroids in rat skeletal muscle cells. J Med Chem. 2011;54(12):4057-4066.

[2]. Dahse I, et al. Effects of (22S,23S)-Homobrassinolide and Related Compounds on Membrane Potential and Transport of Egeria Leaf Cells. Plant Physiol. 1990;93(3):1268-1271.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
643.0±55.0 °C at 760 mmHg

[ Melting Point ]:
193-194ºC

[ Molecular Formula ]:
C₂₉H₅₀O₆

[ Molecular Weight ]:
494.704

[ Flash Point ]:
203.2±25.0 °C

[ Exact Mass ]:
494.360748

[ PSA ]:
107.22000

[ LogP ]:
3.65

[ Vapour Pressure ]:
0.0±4.3 mmHg at 25°C

[ Index of Refraction ]:
1.533

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Akt-dependent anabolic activity of natural and synthetic brassinosteroids in rat skeletal muscle cells.

J. Med. Chem. 54 , 4057-4066, (2011)

Brassinosteroids are plant-derived polyhydroxylated derivatives of 5α-cholestane, structurally similar to cholesterol-derived animal steroid hormones and insect ecdysteroids. In this study, we synthes...

Brassinosteroids protect Lycopersicon esculentum from cadmium toxicity applied as shotgun approach.

Protoplasma 239(1-4) , 3-14, (2010)

Surface-sterilized seeds of two tomato cultivars (cv. K-25 and Sarvodya) were soaked in 100 microM CdCl(2) for 8 h (shotgun approach). The resulting 59-day-old seedlings were sprayed with 10(-8) M of ...

Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide.

Phytochemistry 58(6) , 973-80, (2001)

In this paper we describe the synthesis of two new fluorinated brassinosteroids: (22R,23R)-22,23-dihydroxy-3alpha-fluorostigmastan-6-one and (22R,23R)-22,23-dihydroxy-3beta-fluorostigmastan-6-one. The...