| Identification | More | [Name]
ACETYLSHIKONIN | [CAS]
24502-78-1 | [Synonyms]
1,4-NAPHTHALENEDIONE,2-[1-(ACETYLOXY)-4-METHYL-3-PENTENYL]-5,8-DIHYDROXY-, (R)-
ACETYLSHIKONIN
(+)-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
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)-
(+)-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 | [Molecular Formula]
C18H18O6 | [MDL Number]
MFCD00143538 | [Molecular Weight]
330.33 | [MOL File]
24502-78-1.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [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. |
| Hazard Information | Back Directory | [Chemical Properties]
Acetylshikonin is a biologically active compound with anti-cancer and anti-inflammatory activity, which is isolated from the roots of Lithospermum erythrorhizoma. | [Uses]
Acetylshikonin is the main ingredient of Zicao, which has used in clinics as a traditional Chinese for thousands of years. It exerts anti-obesity and anti-NAFLD effects through the regulation of lipid metabolism and anti-inflammatory effects. Also, it is a 1,4-naphthoquinone pigment extracted from the roots of Lithospermum erythrorhizon with anti-tumor effects. | [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. |
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