Name: Epibrassinolide
SKU: 78821-43-9

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Basic Information

Molecular Structure:
CAS No.:	78821-43-9
Name:	Epibrassinolide

Formula:	C₂₈H₄₈O₆
Molecular Weight:	480.686
Synonyms:	Epin;B-Homo-7-oxaergostan-6-one,2,3,22,23-tetrahydroxy-, (2a,3a,5a,22R,23R)-;24(R)-Epibrassinolide;24-Epibrassinolide;24-epi-Brassinolide;22R,23R,24R-2a,3a,22,23-Tetrahydroxy-B-homo-7-oxa-5a-ergostan-6-one;B 1105;BP 55;
EINECS:	639-387-1
Density:	1.142 g/cm³
Melting Point:	256 °C
Boiling Point:	633.716 °C at 760 mmHg
Flash Point:	202.262 °C
Appearance:	white crystalline powder
Risk Codes:	22-36/37/38
Safety:	22-36/37/39-45
PSA:	107.22000
LogP:	3.39000

Synthetic route

: 72050-71-6
24-epicastasterone

: 78821-43-9
24-epibrassinolide

Conditions

Conditions	Yield
With trifluoroacetyl peroxide In dichloromethane; water at 0℃; for 3h;	83%
With trifluoroacetyl peroxide In chloroform for 2h; Ambient temperature;	80%
With dihydrogen peroxide; trifluoroacetic anhydride In chloroform at 0 - 20℃; for 2h;	80%

: 108942-14-9
(22R,23R,24R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one tetraacetate

: 78821-43-9
24-epibrassinolide

Conditions

Conditions	Yield
With potassium hydroxide for 1h; Heating;	73%

: 124696-45-3
(22E,24R)-B-Homo-7-oxa-5α-ergost-2,22-dien-6-one

A: 78821-42-8
(22S,23S)-24-epibrassinolide

B: 78821-43-9
24-epibrassinolide

Conditions

Conditions	Yield
With 4-methylmorpholine N-oxide; osmium(VIII) oxide In tetrahydrofuran; water; tert-butyl alcohol for 48h; Ambient temperature; Yield given. Yields of byproduct given;

: 1244967-00-7
(22R,23R,24R)-2α,3α,22,23-tetrahydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-6-one 22,23-methylboronate

: 78821-43-9
24-epibrassinolide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylamine-N-oxide / diethylene glycol dimethyl ether / 0.75 h / Reflux 2: Dowex-50W×8, 200–400 mesh, NH4+ form resin View Scheme

: 1493793-17-1
(22R,23R,24R)-2α,3α,22,23-tetrahydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-6-one 22,23-boronate

: 78821-43-9
24-epibrassinolide

Conditions

Conditions	Yield
With Dowex-50W×8, 200-400 mesh, NH4+ form resin

: 57-87-4
Ergosterol

: 78821-43-9
24-epibrassinolide

Conditions

Yield

Multi-step reaction with 5 steps
1.1: methanesulfonyl chloride; pyridine / 20 °C
2.1: ammonia; lithium / tetrahydrofuran / 0.08 h / -78 - 65 °C / Inert atmosphere
2.2: 0.17 h / -78 - 60 °C / Inert atmosphere
2.3: Inert atmosphere
3.1: pyridine hydrochloride; lithium bromide / N,N-dimethyl acetamide / 6 h / 165 °C / Inert atmosphere
4.1: potassium carbonate; osmium(VIII) oxide; potassium hexacyanoferrate(III); 10,11-dihydroquinidine p-chlorobenzoate; methanesulfonamide / water; tert-butyl alcohol
5.1: trifluoroacetyl peroxide
View Scheme

Multi-step reaction with 7 steps
1: sodium carbonate / toluene / 2 h / 10 °C
2: potassium hydrogencarbonate / water; acetone / 3 h / Reflux
3: manganese(IV) oxide / water; methanol / 10 h / 40 °C
4: N,N,N,N,N,N-hexamethylphosphoric triamide; calcium / -5 - 0 °C
5: pyridine hydrochloride; lithium bromide / N,N-dimethyl acetamide / 3 h / 160 °C / Inert atmosphere
6: potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; osmium(VIII) oxide; AD-mix-β / water; tert-butyl alcohol / 144 h / 20 °C
7: trifluoroacetic anhydride; dihydrogen peroxide / chloroform / 2 h / 0 - 20 °C
View Scheme

: 3037-46-5
(22E)-3α,5-cyclo-5α-ergosta-7,22-dien-6β-one

: 78821-43-9
24-epibrassinolide

Conditions

Yield

Multi-step reaction with 4 steps
1.1: ammonia; lithium / tetrahydrofuran / 0.08 h / -78 - 65 °C / Inert atmosphere
1.2: 0.17 h / -78 - 60 °C / Inert atmosphere
1.3: Inert atmosphere
2.1: pyridine hydrochloride; lithium bromide / N,N-dimethyl acetamide / 6 h / 165 °C / Inert atmosphere
3.1: potassium carbonate; osmium(VIII) oxide; potassium hexacyanoferrate(III); 10,11-dihydroquinidine p-chlorobenzoate; methanesulfonamide / water; tert-butyl alcohol
4.1: trifluoroacetyl peroxide
View Scheme

: 3152-46-3
(22E)-3α,5-cyclo-5α-ergosta-22-en-6-one

: 78821-43-9
24-epibrassinolide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine hydrochloride; lithium bromide / N,N-dimethyl acetamide / 6 h / 165 °C / Inert atmosphere 2: potassium carbonate; osmium(VIII) oxide; potassium hexacyanoferrate(III); 10,11-dihydroquinidine p-chlorobenzoate; methanesulfonamide / water; tert-butyl alcohol 3: trifluoroacetyl peroxide View Scheme

: 72050-68-1
24R-methyl-5α-cholesta-2,22-dien-6-one

: 78821-43-9
24-epibrassinolide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; osmium(VIII) oxide; potassium hexacyanoferrate(III); 10,11-dihydroquinidine p-chlorobenzoate; methanesulfonamide / water; tert-butyl alcohol 2: trifluoroacetyl peroxide View Scheme

: (22E,24R)-3α-5-cyclo-5α-ergosta-22-en-6-one

: 78821-43-9
24-epibrassinolide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine hydrochloride; lithium bromide / N,N-dimethyl acetamide / 3 h / 160 °C / Inert atmosphere 2: potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; osmium(VIII) oxide; AD-mix-β / water; tert-butyl alcohol / 144 h / 20 °C 3: trifluoroacetic anhydride; dihydrogen peroxide / chloroform / 2 h / 0 - 20 °C View Scheme

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Specification

The Epibrassinolide, with the CAS registry number 78821-43-9, is also known as 22R,23R,24R-2a,3a,22,23-Tetrahydroxy-B-homo-7-oxa-5a-ergostan-6-one. It belongs to the product categories of Steroids; Bio-Pesticide; Steroids & Hormones - 13C & 2H; Plant Growth Regulator; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C₂₈H₄₈O₆and molecular weight is 480.68. What's more, its systematic name is (3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(2S,3R,4R,5R)-3,4-Dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one.

Physical properties of Epibrassinolide are: (1)ACD/LogP: 3.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.12; (4)ACD/LogD (pH 7.4): 3.12; (5)ACD/BCF (pH 5.5): 138.43; (6)ACD/BCF (pH 7.4): 138.43; (7)ACD/KOC (pH 5.5): 1186.60; (8)ACD/KOC (pH 7.4): 1186.60; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 107.22 Å²; (13)Index of Refraction: 1.536; (14)Molar Refractivity: 131.257 cm³; (15)Molar Volume: 421.056 cm³; (16)Polarizability: 52.035×10^-24cm³; (17)Surface Tension: 45.8 dyne/cm; (18)Density: 1.142 g/cm³; (19)Flash Point: 202.262 °C; (20)Enthalpy of Vaporization: 107.343 kJ/mol; (21)Boiling Point: 633.716 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparationof Epibrassinolide: this chemical can be prepared by (2R,3S,5a,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol at the ambient temperature. This reaction will need reagent CF₃CO₃H and solvent CHCl₃ with the reaction time of 3 hours. The yield is about 53%.

Epibrassinolide can be prepared by (2R,3S,5a,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol at the ambient temperature

Uses of Epibrassinolide: it can be used to produce C₃₄H₅₆O₆. It will need reagent p-TsOH and solvent CH₂Cl₂. The yield is about 82%.

Epibrassinolide can be used to produce C34H56O6

You can still convert the following datas into molecular structure:
(1)SMILES: 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
(2)Std. InChI: 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-/m1/s1
(3)Std. InChIKey: IXVMHGVQKLDRKH-QHBHMFGVSA-N

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Specification