2901-66-8

Basic information

• Product Name: methyl (3beta,16beta,17alpha,18beta,20alpha)-18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate
• Synonyms: methyl (3beta,16beta,17alpha,18beta,20alpha)-18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate;(3β,16β,17α,18β,20α)-11,17-Dimethoxy-18-hydroxyyohimban-16-carboxylic acid methyl ester;(3β,20α)-18β-Hydroxy-11,17α-dimethoxyyohimban-16β-carboxylic acid methyl ester;Reserpic acid methyl;(3β,16β,17α,18β,20α)-18-Hydroxy-11,17-diMethoxy-yohiMban-16-carboxylic Acid Methyl Ester;Methyl reserpinolate;NSC 81464;Reserpic Acid Methyl Ester
• CAS NO: 2901-66-8
• Molecular Formula: C₂₃H₃₀N₂O₅
• Molecular Weight: 414.4947
• EINECS: 220-792-3
• Mol File: 2901-66-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 244.5°C
• Boiling Point: 533.37°C (rough estimate)
• Flash Point: 309.3°C
• Appearance: /
• Density: 1.2138 (rough estimate)
• Vapor Pressure: 1.17E-14mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Dichloromethane, Dimethyl Sulfoxide, Methanol (Slightly)
• PKA: 14.03±0.60(Predicted)
• CAS DataBase Reference: methyl (3beta,16beta,17alpha,18beta,20alpha)-18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3beta,16beta,17alpha,18beta,20alpha)-18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate(2901-66-8)
• EPA Substance Registry System: methyl (3beta,16beta,17alpha,18beta,20alpha)-18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate(2901-66-8)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2901-66-8(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Solid

InChI:InChI=1/C23H30N2O5/c1-28-13-4-5-14-15-6-7-25-11-12-8-19(26)22(29-2)20(23(27)30-3)16(12)10-18(25)21(15)24-17(14)9-13/h4-5,9,12,16,18-20,22,24,26H,6-8,10-11H2,1-3H3

Upstream product

• 50-55-5 reserpine 
• 185811-08-9 (1S,2R,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester 
• 186581-53-3 diazomethane 
• 1173-69-9 rac-18β-hydroxy-11,17α-dimethoxy-20α-yohimban-16β-carboxylic acid-lactone 
• 124-41-4 sodium methylate 
• 1173-69-9 rac-18α-hydroxy-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid-lactone 
• 24815-24-5 rescinnamine 
• 185810-98-4 (1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-5-oxo-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester 
• 185811-02-3 (1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-5-oxo-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester 
• 1054654-18-0 (1S,2S,3R,4aS,13bR,14aS)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester 
• 185811-05-6 (1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester 
• 1053614-44-0 (1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester 

Downstream Products

• 2903-87-9 ent-18α-(2,5-dimethoxy-benzoyloxy)-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid methyl ester 
• 122650-35-5 ent-18α-hippuroyloxy-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid methyl ester 
• 2815-16-9 ent-18α-[(2,5-dimethoxy-phenyl)-acetoxy]-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid methyl ester 
• 119853-39-3 ent-11,17β-dimethoxy-18α-(2-methoxy-3-nitro-benzoyloxy)-15β-yohimban-16α-carboxylic acid methyl ester 
• 3049-82-9 ent-11,17β-dimethoxy-18α-(2-methoxy-5-nitro-benzoyloxy)-15β-yohimban-16α-carboxylic acid methyl ester 
• 2814-98-4 18-(3,4-dihydroxy-benzoyloxy)-11,17-dimethoxy-yohimbane-16-carboxylic acid methyl ester 
• 120174-75-6 ent-11,17β-dimethoxy-18α-((3S)-3r,4c,5t-triacetoxy-cyclohex-1-enecarbonyloxy)-15β-yohimban-16α-carboxylic acid methyl ester 
• 2871-55-8 ent-11,17β-dimethoxy-18α-salicyloyloxy-15β-yohimban-16α-carboxylic acid methyl ester 
• 2814-94-0 ent-18α-(3-hydroxy-4,5-dimethoxy-benzoyloxy)-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid methyl ester 
• 119853-40-6 ent-11,17β-dimethoxy-18α-(3-methoxy-benzoyloxy)-15β-yohimban-16α-carboxylic acid methyl ester 
• 2901-71-5 ent-11,17β-dimethoxy-18α-phenylcarbamoyloxy-15β-yohimban-16α-carboxylic acid methyl ester 
• 119853-43-9 ent-11,17β-dimethoxy-18α-(4-methoxy-benzoyloxy)-15β-yohimban-16α-carboxylic acid methyl ester 
• 119853-41-7 ent-11,17β-dimethoxy-18α-(2-methoxy-benzoyloxy)-15β-yohimban-16α-carboxylic acid methyl ester 
• 2814-90-6 ent-11,17β-dimethoxy-18α-(toluene-4-sulfonyloxy)-15β-yohimban-16α-carboxylic acid methyl ester 

Relevant articles and documents

CHEMOTHERAPEUTIC FOR INDUCING AN MSH2-DEPENDENT APOPTOTIC PATHWAY

A method of treating cancer in a subject in need thereof comprises administering said subject reserpine, yohimbine, an analog thereof, or a pharmaceutically acceptable salt or prodrug thereof, in an amount effective to treat the cancer. Compounds and compositions useful for carrying out the method are also described.

A PROCESS FOR THE SEMISYNTHESIS OF DESERPIDINE

The present invention relates to an efficient procedure for the synthesis of deserpidine (Ia), starting from reserpic acid lactone (II) via the intermediate 11-O-demethyl reserpic acid lactone (III).

Total synthesis of (-)-reserpine using the chiron approach

A highly stereocontrolled synthesis of ring D/E precursor to reserpine has been developed starting from (-)-quinic acid as a chiral template. The total synthesis of (-)-reserpine is described through the cyclization of an immonium lactam intermediate.