Home > Name List By other > (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5, 8a-dimethyl-2-methylidene-3,4,4a,6,7, 8-hexahydro-1H-naphthal...

CAS No 5508-58-7 , (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,
8a-dimethyl-2-methylidene-3,4,4a,6,7,
8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one

  • Name: (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,
    8a-dimethyl-2-methylidene-3,4,4a,6,7,
    8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
  • Synonyms: CHEBI:65408; 5508-58-7;(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,
    8a-dimethyl-2-methylidene-3,4,4a,6,7,
    8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one;Andrographis;
  • CAS Registry Number:
  • Melting Point: 229-232 ºC
  • Density: 1.21g/cm3
  • Refractive index: 1.567
  • Alpha: -126 º (C=1.5,HAC)
  • Safety Statements: S22;S24/25
  • Hazard Symbols: Xn
  • EINECS: 226-852-5
  • Molecular Weight: 350.4492
  • InchiKey: BOJKULTULYSRAS-OTESTREVSA-N
  • InChI: InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,
    3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,
    2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
  • Risk Statements: S22;S24/25
  • Molecular Formula: C20H30O5
  • Molecular Structure:CAS No:5508-58-7 (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,<br />8a-dimethyl-2-methylidene-3,4,4a,6,7,<br />8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one

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References of (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,
8a-dimethyl-2-methylidene-3,4,4a,6,7,
8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
Title: Andrographolide
CAS Registry Number: 5508-58-7
CAS Name: (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
Synonyms: 3a,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid g-lactone
Molecular Formula: C20H30O5
Molecular Weight: 350.45
Percent Composition: C 68.54%, H 8.63%, O 22.83%
Literature References: Main bitter constituent and medicinally active principle isolated from the leaves of andrographis, q.v. Isoln: M. K. Gorter, Rec. Trav. Chim. 30, 151 (1911). Rapid isoln method: M. Rajani et al., Pharmaceut. Biol. 38, 204 (2000). Characterization: D. Chakravarti, R. N. Chakravarti, J. Chem. Soc. 1952, 1697; R. Schwyzer et al., Helv. Chim. Acta 34, 652 (1951). Structure: M. P. Cava, B. Weinstein, Chem. Ind. (London) 1959, 851. Revised structure: M. P. Cava et al., ibid. 1963, 167; M. P. Cava et al., Tetrahedron 21, 2617 (1965). X-ray crystallographic analysis: T. Fujita et al., Chem. Pharm. Bull. 32, 2117 (1984). HPLC determn in plant material: A. Sharma et al., Phytochem. Anal. 3, 129 (1992). Determn in Chinese medicinal prepns: Z. Yanfang et al., J. Pharm. Biomed. Anal. 40, 157 (2006). Mechanism of anti-inflammatory action: Y.-F. Xia et al., J. Immunol. 173, 4207 (2004). Clinical pharmacokinetics and bioavailability from herbal preparations: A. Panossian et al., Phytomedicine 7, 351 (2000).
Properties: Colorless plates from ethanol or methanol, mp 218° (dec) (Gorter). Also reported as mp 218-221° (Fujita). [a]D25 -96.2° (c = 1.00 in C5H5N). d421 1.2317. uv max (alcohol): 223 nm (log e 4.09). Sparingly sol in water; sol in acetone, methanol, chloroform, ether.
Melting point: mp 218° (dec) (Gorter); mp 218-221° (Fujita)
Optical Rotation: [a]D25 -96.2° (c = 1.00 in C5H5N)
Absorption maximum: uv max (alcohol): 223 nm (log e 4.09)
Density: d421 1.2317
 
Derivative Type: Triacetyl derivative
Molecular Formula: C26H36O8
Molecular Weight: 476.56
Percent Composition: C 65.53%, H 7.61%, O 26.86%
Properties: Fine needles from alcohol + ether, mp 126-126.5°.
Melting point: mp 126-126.5°