Acetylshikonin

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Names

[ CAS No. ]:
24502-78-1

[ Name ]:
Acetylshikonin

[Synonym ]:
1'O-acetylshikonin
(1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl acetate
1,4-Naphthalenedione, 2-[(1R)-1-(acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy-
O-Acetylshikonin
Shikonin acetate
acethylshikonin
1,4-Naphthalenedione, 2-[1- (acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-, (R)-
(1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate
Acetylshikonin: 1,4-Naphthalenedione,2-[1-(acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-, (R)-,
Shikonin,acetyl
MFCD00143538
acetyl shikonin
(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl acetate

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
553.2±50.0 °C at 760 mmHg

[ Melting Point ]:
86°C

[ Molecular Formula ]:
C18H18O6

[ Molecular Weight ]:
330.332

[ Flash Point ]:
201.3±23.6 °C

[ Exact Mass ]:
330.110352

[ PSA ]:
100.90000

[ LogP ]:
4.57

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

[ Index of Refraction ]:
1.602

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QL8001000
CHEMICAL NAME :
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)-
CAS REGISTRY NUMBER :
24502-78-1
LAST UPDATED :
199112
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C18-H18-O6
MOLECULAR WEIGHT :
330.36
WISWESSER LINE NOTATION :
L66 BV EVJ CYOV1&2UY1&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 :
41 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

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • Shikonine
  • acetic acid
  • Ethanoic anhydride

DownStream

  • Shikonine
  • naphthazarin-dimethyl-hydrofuran hdfr
  • cycloalkannin leucoacetate

Related Compounds

  • Acetylshikonin
  • (R,S)-Acetylshikonin-d7
  • N-[3-(morpholin-4-ylmethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide
  • n-{3-[(Dimethylamino)methyl]phenyl}-4-[(4-phenylquinazolin-2-yl)amino]benzamide
  • N-(2,6-dimethylphenyl)-4-{[4-(1H-indol-5-yl)quinazolin-2-yl]amino}benzamide
  • N-(5-amino-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide
  • N-(2,6-dimethylphenyl)-4-[(4-methylquinazolin-2-yl)amino]benzamide
  • n-(2,6-Dimethylphenyl)-2-(methyloxy)-4-[(4-phenylquinazolin-2-yl)amino]benzamide
  • 2-chloro-N-(2,6-dimethylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide
  • N-[2-methyl-5-(1-morpholin-4-ylethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide
  • N-[2,5-bis(hydroxymethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide
  • n-{1-[(2,6-Dichlorophenyl)carbonyl]piperidin-4-yl}-4-phenylquinazolin-2-amine