Home > Name List By m > methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4, 5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20, 21-dodecahydr...

CAS No 50-55-5 , methyl
(1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,
5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,
21-dodecahydroyohimban-19-carboxylate

  • Name: methyl
    (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,
    5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,
    21-dodecahydroyohimban-19-carboxylate
  • Synonyms: Hiserpia; Sandril; Serpalan; Serpate; Serpanray; Apoplon;Serpasil; Rau-Sed; Serpivite;methyl
    (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,
    5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,
    21-dodecahydroyohimban-19-carboxylate;
  • CAS Registry Number:
  • Transport: UN 1219
  • Melting Point: 265 ºC (DEC.)
  • Flash Point: 377.2°C
  • Boiling Point: 700.1°Cat760mmHg
  • Density: 1.32g/cm3
  • Refractive index: 177 ° (C=1, DMF)
  • Water Solubility: Insoluble
  • Safety Statements: R10;R36;R67
  • Hazard Symbols: Xi: Irritant;
  • Flash Point: 377.2°C
  • EINECS: 200-047-9
  • Molecular Weight: 608.6787
  • InchiKey: QEVHRUUCFGRFIF-MDEJGZGSSA-N
  • InChI: InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-
    11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29
    (21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,
    1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
  • Risk Statements: S26
  • Molecular Formula: C33H40N2O9
  • Molecular Structure:CAS No:50-55-5 methyl<br />(1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,<br />5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,<br />21-dodecahydroyohimban-19-carboxylate

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References of methyl
(1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,
5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,
21-dodecahydroyohimban-19-carboxylate
Title: Reserpine
CAS Registry Number: 50-55-5
CAS Name: (3b,16b,17a,18b,20a)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
Synonyms: 3,4,5-trimethoxybenzoyl methyl reserpate
Trademarks: Rivasin (Solvay); Serpasil (Novartis)
Molecular Formula: C33H40N2O9
Molecular Weight: 608.68
Percent Composition: C 65.12%, H 6.62%, N 4.60%, O 23.66%
Literature References: Indole alkaloid found in Rauwolfia spp. Isoln from the roots of Rauwolfia serpentina L. Benth., Apocynaceae: J. M. Müller et al., Experientia 8, 338 (1952); and structural studies: L. Dorfman et al., Helv. Chim. Acta 37, 59 (1954); N. Neuss et al., J. Am. Chem. Soc. 76, 2463 (1954). Stereochemistry: P. E. Aldrich et al., ibid. 81, 2481 (1959); Y. Ban, O. Yonemitsu, Tetrahedron 20, 2877 (1964). First total synthesis: R. B. Woodward et al., J. Am. Chem. Soc. 78, 2023 (1956); eidem, Tetrahedron 2, 1 (1958). Review of total syntheses: F.-E. Chen, J. Huang, Chem. Rev. 105, 4671-4706 (2005). Comprehensive description: R. E. Schirmer, Anal. Profiles Drug Subs. 4, 384-430 (1975). Review: A. Scriabine, Ed. in Pharmacology of Antihypertensive Drugs (Raven, New York, 1980) pp 119-125. Review of carcinogenicity studies: IARC Monographs 10, 217-229 (1976); R. M. Diener et al., Toxicol. Pathol. 8, 1-21 (1980).
Properties: Long prisms from dil acetone, dec 264-265° (dec 277-277.5° in evac tube). [a]D23 -118° (CHCl3); [a]D26 -164° (c = 0.96 in pyridine); [a]D26 -168° (c = 0.624 in DMF). uv max (CHCl3): 216, 267, 295 nm (e 61700, 17000, 10200). Weak base. pK 6.6. Very sparingly sol in water. Freely sol in chloroform (~1 g/6 ml), methylene chloride, glacial acetic acid. Sol in benzene, ethyl acetate. Slightly sol in acetone, methanol, alcohol (1 g/1800 ml), ether, and in aq solns of acetic and citric acids.
pKa: pK 6.6
Optical Rotation: [a]D23 -118° (CHCl3); [a]D26 -164° (c = 0.96 in pyridine); [a]D26 -168° (c = 0.624 in DMF)
Absorption maximum: uv max (CHCl3): 216, 267, 295 nm (e 61700, 17000, 10200)
 
Derivative Type: Hydrochloride hydrate
Molecular Formula: C33H40N2O9.HCl.H2O
Molecular Weight: 663.15
Percent Composition: C 59.77%, H 6.54%, N 4.22%, O 24.13%, Cl 5.35%
Properties: Crystals, dec 224°.
 
CAUTION: Reserpine is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-228.
Therap-Cat: Antihypertensive.
Therap-Cat-Vet: Hypotensive, tranquilizer. Has been used to prevent aortic rupture in turkeys.
Keywords: Antihypertensive; Reserpine Derivatives.