Structural Formula Vector Image
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
Additional Names: 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°

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