Introduction：Basic information about CAS 24502-78-1|Acetylshikonin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Acetylshikonin |
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| CAS Number | 24502-78-1 | Molecular Weight | 330.332 |
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| Density | 1.3±0.1 g/cm3 | Boiling Point | 553.2±50.0 °C at 760 mmHg |
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| Molecular Formula | C18H18O6 | Melting Point | 86°C |
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| MSDS | / | Flash Point | 201.3±23.6 °C |
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Names
| Name | acetylshikonin |
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| Synonym | More Synonyms |
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Acetylshikonin BiologicalActivity
| 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]. |
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| Related Catalog | Research Areas >>CancerSignaling Pathways >>Metabolic Enzyme/Protease >>Cytochrome P450Research Areas >>Inflammation/ImmunologySignaling Pathways >>Neuronal Signaling >>AChE |
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| Target | IC50: 1.4-4.0 μM (all P450s)[2] AChE[3] |
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| 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. |
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Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
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| Boiling Point | 553.2±50.0 °C at 760 mmHg |
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| Melting Point | 86°C |
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| Molecular Formula | C18H18O6 |
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| Molecular Weight | 330.332 |
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| Flash Point | 201.3±23.6 °C |
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| Exact Mass | 330.110352 |
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| PSA | 100.90000 |
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| LogP | 4.57 |
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| Vapour Pressure | 0.0±1.6 mmHg at 25°C |
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| Index of Refraction | 1.602 |
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| InChIKey | WNFXUXZJJKTDOZ-UAVYNJCWSA-N |
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| SMILES | CC(=O)OC(CC=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O |
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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 DATAACUTE 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
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Safety Information
| Hazard Codes | Xi |
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| Risk Phrases | R36/37/38 |
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| Safety Phrases | S26-S36/37/39 |
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Synonyms
| 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 |
