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ACETYLSHIKONIN

ACETYLSHIKONIN Structure
CAS No.
24502-78-1
Chemical Name:
ACETYLSHIKONIN
Synonyms
Nsc110199;ACETYLSHIKONIN;Shikonin acetate;Shikonin, acetyl;O-Acetylshikonin;(R)-acetyl shikonin;3-pentenyl]-5,8-dihydroxy-,(R)-;Racemic Acetyl Shikonin Labeled d7;1,4-Naphthalenedione,2-[1-(acetyloxy)-4-methyl-;2,3-dimethoxybenzoic acid 2-(dimethylamino)ethyl ester hydrochloride
CBNumber:
CB8317267
Molecular Formula:
C18H18O6
Molecular Weight:
330.33
MOL File:
24502-78-1.mol
MSDS File:
SDS
Modify Date:
2024/7/2 8:55:27

ACETYLSHIKONIN Properties

Melting point 86°C
Boiling point 553.2±50.0 °C(Predicted)
Density 1.326±0.06 g/cm3(Predicted)
storage temp. 4°C, protect from light
solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form Powder
pka 7.12±0.20(Predicted)
color Brown to khaki
Stability Hygroscopic
LogP 2.700 (est)
CAS DataBase Reference 24502-78-1(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Risk Statements  36/37/38
Safety Statements  26-36/37/39
Toxicity mouse,LD50,intraperitoneal,41mg/kg (41mg/kg),BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)BEHAVIORAL: ATAXIA,Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 73, Pg. 193, 1977.

ACETYLSHIKONIN Chemical Properties,Uses,Production

Chemical Properties

Acetylshikonin is a biologically active compound with anti-cancer and anti-inflammatory activity, which is isolated from the roots of Lithospermum erythrorhizoma.

Biological Activity

Acetylshikonin is one naphthoquinone derivative isolated from the Lithospermum erythrorhizon, exhibits weak cytotoxicity against human umbilical vein endothelial cells (HUVECs) with IC50 of over 20 microM, exhibits the antiangiogenic and antitumorigenic effects by suppressing proliferation and angiogenic factors.
Acetylshikonin inhibits the generation of NADPH oxidase complex in the activation of respiratory burst of PMNs, but does not directly inhibit the activity of NADPH oxidase already generated.
Certain shikonin derivatives(such as Acetyl shikonin) act as modulators of the Nur77-mediated apoptotic pathway and identify a new shikonin-based lead that targets Nur77 for apoptosis induction.
Acetylshikonin, shikonin, and alkannin have accelerative effect on the proliferation of granulation tissue in rats.
Acetylshikonin isolated from Arnebia euchroma (Royle) Johnst cell suspension cultures exhibits specific in vivo and in vitro antitumor effects.
Acetylshikonin has inhibitory effect on the edematous response is due neither to the release of steroid hormones from the adrenal gland nor to the glucocorticoid activity, but probably partly to the suppression of mast cell degranulation and partly to protection of the vasculature from mediator challenge.
Acetylshikonin induces apoptosis of hepatitis B virus X protein-expressing human hepatocellular carcinoma cells via endoplasmic reticulum stress.

ACETYLSHIKONIN Preparation Products And Raw materials

Raw materials

Preparation Products

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(+)-5,8-Dihydroxy-2-[(R)-1-acetoxy-4-methyl-3-pentenyl]-1,4-naphthoquinone (R)-1-(1,4-Dihydro-5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methyl-3-pentenyl=acetate 2-[(R)-1-Acetoxy-4-methyl-3-pentenyl]-5,8-dihydroxy-1,4-naphthoquinone O-Acetylshikonin 1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)- Nsc110199 Shikonin, acetyl Shikonin acetate (+)-5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone2-acet 4-naphthalenedione,2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-( 4-naphthoquinone,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-2-acetate 1,4-NAPHTHALENEDIONE,2-[1-(ACETYLOXY)-4-METHYL-3-PENTENYL]-5,8-DIHYDROXY-, (R)- ACETYLSHIKONIN (R)-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)-, 1,4-Naphthalenedione,2-[1-(acetyloxy)-4-methyl- 3-pentenyl]-5,8-dihydroxy-,(R)- Racemic Acetyl Shikonin Labeled d7 2,3-dimethoxybenzoic acid 2-(dimethylamino)ethyl ester hydrochloride 1,4-Naphthalenedione, 2-[(1R)-1-(acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy- (R)-acetyl shikonin 24502-78-1 Miscellaneous Natural Products