Detail of "517-89-5"

CAS Number:
517-89-5
Name:
1,4-Naphthalenedione,5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-
Superlist Name:
Shikonin
Molecular Structure:
Formula:
C₁₆H₁₆O₅
Molecular Weight:
288.30
Synonyms:
1,4-Naphthalenedione,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-;1,4-Naphthalenedione,5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]- (9CI);1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-(8CI);Shikonin (6CI);(+)-Shikonin;C.I. 75535;Isoarnebin 4;NSC 252844;Shikonin S;Shikonine;Tokyo Violet;
Density:
1.373 g/cm³
Melting Point:
147 °C
Boiling Point:
567.4 °C at 760 mmHg
Flash Point:
311 °C
Solubility:
insoluble in water
Risk Codes:
20/21/22
Safety:
26-36/37/39 Details

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Reversed-phase ion-pair high-performance liquid chromatography of naphthazarins: Reversed-phase ion-pair high-performance liquid chromatography of naphthazarins. Nickel, Stanley L.; Carroll, Thomas F. (Coll. Pharm., Univ. Toledo, Toledo, OH 43606, USA). J. Chromatogr., 295(2), 521-5 (English) 1984. CODEN: JOCRAM. ISSN: 0021-9673. DOCUMENT TYPE: Journal CA Section: 64 (Pharmaceutical Analysis) Shikonin [517-89-5] and alkannin [517-88-4] naphthazarin pigments were sepd. on a MicroPak MCH-10 column with a mobile phase of solvent A [(0.01M Me4N+Cl- or nonylamine (ion-pairing agents) in MeCN-MeOH (5:12)]-solvent B (0.01M Me4N+Cl or nonylamine in H2O contg. 0.01M K2HPO4 adjusted to pH 3.0 with H3PO4), temp, 70°, flow rate 2 mL/min and detection at 520 min. Sovaleryl and a-methyl-n-Bu derivs. could not be sepd. Benzene exts. of Macrotomia euchroma plant material and Lithospermum erythrorhizon tissue culture were analyzed for the compds.

Pharmacological studies on crude plant drugs, Shikon and Tooki: Pharmacological studies on crude plant drugs, Shikon and Tooki. (II). Shikonin and Acetylshikonin. Hayashi, Motohide (Sch. Med., Gifu Univ., Gifu, Japan). Nippon Yakurigaku Zasshi, 73(2), 193-203 (Japanese) 1977. CODEN: NYKZAU. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacodynamics) The LD50 values of shikonin (I) [517-89-5] and acetylshikonin (II) [24502-78-1] were 20 and 41 mg/kg, i.p., resp., and >1000 mg/kg, orally. Weak analgesic effects were obsd. in mice. Moderate antipyretic and hypothermic actions were also obsd. Pos. chronotropic and inotropic actions in isolated guinea pig atrium were obsd. at >10-4 g/mL. Vasoconstriction was obsd. in isolated rabbit ear vessel at 10-5 g/mL. These cardiovascular actions were not affected by pretreatment with tolazoline and propranolol. These drugs (100 mg/kg, orally) inhibited histamine-induced vascular permeability in rats. The antiinflammatory activity of I and II was similar to that of phenylbutazone. Shiunko, an ointment prepn. of I, appeared effective for the treatment of cutaneous injuries.