Shikonine

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Names

[ CAS No. ]:
517-89-5

[ Name ]:
Shikonine

[Synonym ]:
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-naphthoquinone
1,4-Naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-
1,4-Naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]-
MFCD00075680
Shikonin
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthoquinone
(+)-Alkannin
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
567.4±50.0 °C at 760 mmHg

[ Melting Point ]:
147ºC

[ Molecular Formula ]:
C16H16O5

[ Molecular Weight ]:
288.295

[ Flash Point ]:
311.0±26.6 °C

[ Exact Mass ]:
288.099762

[ PSA ]:
94.83000

[ LogP ]:
4.35

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.642

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QL8000200
CHEMICAL NAME :
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-
CAS REGISTRY NUMBER :
517-89-5
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C16-H16-O5
MOLECULAR WEIGHT :
288.32
WISWESSER LINE NOTATION :
L66 BV EVJ CYQ2UY1&1 GQ JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 73,193,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Behavioral - ataxia
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 73,193,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PJPHEO Pakistan Journal of Pharmacology. (c/o Univ. of Karachi, Faculty of Pharmacy, Karachi, 32, Pakistan) V.1- 1984- Volume(issue)/page/year: 3(1-2),43,1986

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S26-S36/37/39

[ HS Code ]:
2914690090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • (R)-4-methyl-1-(naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine)-4-yl)pent-3-en-1-ol
  • 4-BROMONAPHTHO[1,8-DE:4,5-D'E']BIS([1,3]DIOXINE)
  • NAPHTHO[1,8-DE:4,5-D'E']BIS([1,3]DIOXINE)
  • 2-SULFO-1,4-BENZENEDICARBOXYLIC ACID 1,4-DIMETHYL ESTER, SODIUM SALT
  • 4-methylpent-3-enoic acid
  • 4-Methyl-3-pentenenitrile
  • 6-methyl-hepta-1,5-dien-3-one

DownStream

  • Acetylshikonin
  • 5,8-dihydroxy-2-(4-methylpentyl)naphthalene-1,4-dione

Customs

[ HS Code ]: 2914690090

[ Summary ]:
2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Related Compounds

  • 3-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-N-methylpentanamido]propanoic acid
  • (2S,3S)-2-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanamido]-3-methylpentanoic acid
  • 1-[3-(5-Amino-4-methylpiperidin-2-yl)phenyl]ethan-1-one
  • 1-{3-[3-(Aminomethyl)-6-methylpiperidin-2-yl]phenyl}ethan-1-one
  • 2-{4-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-1,3-thiazole-4-carbonyl]morpholin-2-yl}acetic acid
  • 4-(1-{2-[1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)ethyl]-1,3-thiazol-4-yl}-N-methylformamido)butanoic acid
  • 4-[(2-bromo-4-chlorophenyl)carbamoyl]-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid
  • 2-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-dimethylpropanamido]-3,3,3-trifluoro-2-methylpropanoic acid
  • 3-cyclopropyl-3-[5-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanamido]propanoic acid
  • (3R)-1-[4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methoxybutanoyl]piperidine-3-carboxylic acid
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