5945-86-8

Basic information

• Product Name: NIMBIN
• Synonyms: NIMBIN;NIMBINH;(17α)-6α-Acetoxy-7α,15β:21,23-diepoxy-4β,8-dimethyl-1-oxo-18,24-dinor-11,12-seco-5α-chola-2,13,20,22-tetrene-4α,11-dicarboxylic acid dimethyl ester;18,24-Dinor-11,12-secochola-2,13,20,22-tetraene-4,11-dicarboxylic acid, 6-(acetyloxy)-7,15:21,23-diepoxy-4,8-dimethyl-1-oxo-, dimethyl ester, (4alpha,5alpha,6alpha,7alpha,15beta,17alpha)-;2H-Cyclopenta(B)naphtho(2,3-D)furan-10-acetic acid, 5-(acetyloxy)-2-(3-furanyl)-3,3A,4A,5,5A,6,9,9A,10,10A-decahydro-6-(methoxycarbonyl)-1,6,9A,10A-tetamethyl-9-oxo-, methyl ester, (2R,3ar,4as,5R,5ar,6R,9ar,10S,10ar)-;Nimbin ,95%;(4α,5α,6α,7α,15β,17α)-6-(Acetyloxy)-7,15:21,23-Diepoxy-4,8-diMethyl-1-oxo- 18,24-dinor-11,12-secochola-2,13,20,22-tetraene-4,11-dicarboxylic Acid DiMethyl Ester;5-(Acetyloxy)-2-(3-furanyl)-3,3a,4a,5,5a,6,9,9a,10,10a- decahydro-6-(Methoxycarbonyl)-1,6,9a,10a-tetraMethyl-9-oxo-2H-cyclopenta[b]naphtho[2,3-d]furan-10-acetic Acid
• CAS NO: 5945-86-8
• Molecular Formula: C₃₀H₃₆O₉
• Molecular Weight: 540.6
• Product Categories: Heterocycles;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5945-86-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 197-199°C (dec.)
• Boiling Point: 606.1oC at 760 mmHg
• Flash Point: 320.4oC
• Appearance: /
• Density: 1.27g/cm3
• Vapor Pressure: 1.22E-14mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: NIMBIN(CAS DataBase Reference)
• NIST Chemistry Reference: NIMBIN(5945-86-8)
• EPA Substance Registry System: NIMBIN(5945-86-8)

Safety Data

• Hazardous Substances Data: 5945-86-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Definition

ChEBI: A limonoid found in Azadirachta indica.

InChI:InChI=1/C30H36O9/c1-15-18(17-9-11-37-14-17)12-19-23(15)30(5)20(13-22(33)35-6)29(4)21(32)8-10-28(3,27(34)36-7)25(29)24(26(30)39-19)38-16(2)31/h8-11,14,18-20,24-26H,12-13H2,1-7H3/t18-,19-,20-,24-,25+,26-,28-,29+,30-/m1/s1

Synthetic route

Nimbin (5945-86-8) + fipronilβ-cyclodextrin (7585-39-9) → C30H36O9*C42H70O35 (1240044-25-0)

Conditions	Yield
In ethanol; water at 20℃; for 120h;	91%

2,2',2'',2''',2'''',2''''',2''''''-heptakis(O-(2-hydroxypropyl))-β-cyclodextrin (770728-81-9) + Nimbin (5945-86-8) → C30H36O9*C63H112O42 (1240044-29-4)

Conditions	Yield
In ethanol; water at 20℃; for 120h;	90%

heptakis(2,6-di-O-methyl)cyclomaltoheptaose (51166-71-3) + Nimbin (5945-86-8) → C30H36O9*C56H98O35 (1240044-32-9)

Conditions	Yield
In ethanol; water at 20℃; for 120h;	82%

Nimbin (5945-86-8) + 2,3,6-trimethyl-beta-cyclodextrin (55216-11-0) → C30H36O9*C63H112O35 (1240044-34-1)

Conditions	Yield
In ethanol; water at 20℃; for 120h;	80%

Nimbin (5945-86-8) → nimbinlactone

Conditions	Yield
With N-Bromosuccinimide In methanol for 0.00416667h; microwave irradiation;	76%

Nimbin (5945-86-8) → 6-De-O-acetylnimbin (18609-16-0)

Conditions	Yield
With ethylenediamine In methanol for 0.116667h; Microwave irradiation;	75%

Nimbin (5945-86-8) → 6-deacetylnimbinene (78916-55-9) + 7,15;21,23-diepoxy-6-hydroxy-4,8-dimethyl-1-oxo-12,13-seco-24-nor-chola-2,13,20,22-tetraen-12-oic acid methyl ester

Conditions	Yield
With potassium hydroxide Behandeln des erhaltenen Saeure-Gemisches mit Diazomethan in Aether; stereoisomer(ic) of mp: 158-160 degree;
With potassium hydroxide Behandeln des erhaltenen Saeure-Gemisches mit Diazomethan in Aether; stereoisomer(ic) of mp: 153-154 degree;

Nimbin (5945-86-8) → 7α,15β;21,23-diepoxy-6α-hydroxy-4β,8-dimethyl-1-oxo-11,13-seco-C,24-dinor-5α,17βH-chola-2,13,20,22-tetraene-4α,11-dicarboxylic acid

Conditions	Yield
With potassium hydroxide

Nimbin (5945-86-8) → 7α,15β;21,23-diepoxy-6α-hydroxy-4β,8-dimethyl-1-oxo-11,13-seco-C,24-dinor-5α,17βH-chola-2,13,20,22-tetraene-4α,11-dicarboxylic acid-4-methyl ester (5866-30-8)

Conditions	Yield
With potassium hydroxide
With methanol; potassium hydrogencarbonate

Nimbin (5945-86-8) → 6α-acetoxy-7α,15β;21,23-diepoxy-4β,8-dimethyl-1-oxo-11,13-seco-C,24-dinor-5α,17βH,20ξH-chol-13-ene-4α,11-dicarboxylic acid dimethyl ester (4801-85-8)

Conditions	Yield
With methanol; palladium on activated charcoal Hydrogenation;
With palladium on activated charcoal; ethyl acetate Hydrogenation;

Nimbin (5945-86-8) → 6α-acetoxy-7α,15β;21,23-diepoxy-4β,8-dimethyl-1-oxo-11,13-seco-C,24-dinor-5α,17βH-chola-13,20,22-triene-4α,11-dicarboxylic acid dimethyl ester (73264-01-4)

Conditions	Yield
With methanol; palladium on activated charcoal Hydrogenation;

Nimbin (5945-86-8) → Nimbinolide + Isonimbinolide

Conditions	Yield
With oxygen In benzene for 0.5h; Oxidation; UV-irradiation;	A 32 mg B 8 mg

acetic acid (64-19-7) + Nimbin (5945-86-8) + platinum → compound C29H38(?)O8

Conditions	Yield
Hydrogenation;

methanol (67-56-1) + Nimbin (5945-86-8) + palladium/charcoal → dihydronimbin

Conditions	Yield
Hydrogenation;

methanol (67-56-1) + Nimbin (5945-86-8) + palladium/charcoal → hexahydronimbin

Conditions	Yield
Hydrogenation;

Nimbin (5945-86-8) → 7,15;21,23-diepoxy-6-hydroxy-4,8-dimethyl-1-oxo-12,13-seco-24-nor-chola-2,13,20,22-tetraen-12-oic acid methyl ester + stereoisomer(ic) of mp: 153-154 degree

Conditions	Yield
With potassium hydroxide Behandeln des erhaltenen Saeure-Gemisches mit Diazomethan in Aether; stereoisomer(ic) of mp: 158-160 degree;

Nimbin (5945-86-8) → 6-deacetylnimbinene (78916-55-9) + stereoisomer(ic) of mp: 158-160 degree and of mp: 153-154 degree

Conditions	Yield
With potassium hydroxide Behandeln des erhaltenen Saeure-Gemisches mit Diazomethan in Aether;

Nimbin (5945-86-8) → 7,15;21,23-diepoxy-6-hydroxy-4,8-dimethyl-1-oxo-12,13-seco-24-nor-chola-2,13,20,22-tetraen-12-oic acid methyl ester + stereoisomer(ic) of mp: 158-160 degree

Conditions	Yield
With potassium hydroxide Behandeln des erhaltenen Saeure-Gemisches mit Diazomethan in Aether; stereoisomer(ic) of mp: 153-154 degree;

Nimbin (5945-86-8) → isonimbin

Conditions	Yield
With boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide In chloroform at -15℃; for 16h;

Downstream Products

• 78916-55-9 6-deacetylnimbinene 
• 5866-30-8 7α,15β;21,23-diepoxy-6α-hydroxy-4β,8-dimethyl-1-oxo-11,13-seco-C,24-dinor-5α,17βH-chola-2,13,20,22-tetraene-4α,11-dicarboxylic acid-4-methyl ester 
• 1240044-34-1 C₃₀H₃₆O₉*C₆₃H₁₁₂O₃₅ 
• 1240044-32-9 C₃₀H₃₆O₉*C₅₆H₉₈O₃₅ 
• 18609-16-0 6-De-O-acetylnimbin