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Acetylshikonin

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

Biological Activity

[Description]:

Acetylshikonin, derived from the root of Lithospermum erythrorhizon, has anti-cancer and antiinflammation activity. Acetylshikonin is a non-selective cytochrome P450 inhibitor against all P450s (IC50 values range from 1.4-4.0 μM). Acetylshikonin is an AChE inhibitor and exhibits potent antiapoptosis activity[1][2][3].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450
Research Areas >> Inflammation/Immunology
Signaling Pathways >> Neuronal Signaling >> AChE

[Target]

IC50: 1.4-4.0 μM (all P450s)[2] AChE[3]


[References]

[1]. Park SH, et al. Identification of acetylshikonin as the novel CYP2J2 inhibitor with anti-cancer activity in HepG2 cells. Phytomedicine. 2017 Jan 15;24:134-140.

[2]. Shon JC, et al. Acetylshikonin is a novel non-selective cytochrome P450 inhibitor. Biopharm Drug Dispos. 2017 Dec;38(9):553-556.

[3]. Wang Y, et al. Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells. Evid Based Complement Alternat Med. 2013;2013:937370.

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

DownStream

Related Compounds