1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)-
Acetyl Shikonin
CAS: 24502-78-1
Molecular Formula: C18H18O6
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)- - Names and Identifiers
| Name | Acetyl Shikonin |
| Synonyms | Nsc110199 Acetylshikonin Acetyl Shikonin O-Acetylshikonin Shikonin, acetyl Shikonin acetate 2-[(R)-1-Acetoxy-4-methyl-3-pentenyl]-5,8-dihydroxy-1,4-naphthoquinone (+)-5,8-Dihydroxy-2-[(R)-1-acetoxy-4-methyl-3-pentenyl]-1,4-naphthoquinone 1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)- 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate (1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate |
| CAS | 24502-78-1 |
| InChI | InChI=1/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3/t15-/m1/s1 |
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)- - Physico-chemical Properties
| Molecular Formula | C18H18O6 |
| Molar Mass | 330.33 |
| Density | 1.326±0.06 g/cm3(Predicted) |
| Melting Point | 86°C |
| Boling Point | 553.2±50.0 °C(Predicted) |
| Flash Point | 201.3°C |
| Solubility | DMSO:2 mg/mL (6.05 mM) |
| Vapor Presure | 7.56E-13mmHg at 25°C |
| Appearance | Red crystalline powder |
| pKa | 7.12±0.20(Predicted) |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.601 |
| MDL | MFCD00143538 |
| Physical and Chemical Properties | Red crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from shikonin. |
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)- - Risk and Safety
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 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. |
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)- - Reference
| Reference Show more | 1. Dong Na Gao Zhao Jun Qu Xiaolan et al. Simultaneous Determination of Five Naphthoquinones in Taishan Arnebia euphratica by HPLC [J]. Journal of Taishan Medical College 2019 40(05):336-338. 2. Sun Jianwen Wen Xianchun Cai Defu et al. Simultaneous Determination of Shikonin, Acetyl Shikonin and β-Dimethylacryloyl Shikonin in Xinjiang Shikonin by RP-HPLC Method [J]. 2018 v.29 of Chinese Pharmacy; No.622(04):455-457. 3. Ma Liuchun, Ma Shengjun, Zhu Jinfang, Yang Jianbo, Zhou Mingcong, Song Xiaoyu. Establishment of HPLC Fingerprint, Chemical Pattern Recognition Analysis and Content Determination of Areach in Xinjiang [J]. Chinese Pharmacy, 2020,31(14):1732-1738. 4. Zhang Lei, Zhang Aiqin, Wang Man, et al. Study on Capillary Electrophoresis Fingerprint of Arnebia euphratica in Xinjiang [J]. Analytical Chemistry, 2017(11). 5. Gao Zhaojun, Liu Qiuyue, Qu Xiaolan, et al.. Comparative Study on HPLC Fingerprints of Arnebia ischaensis and Arnebia sinensis [J]. Chinese Modern Applied Pharmacy, 2019, 036(010):1193-1196. 6. Chen Hong. Synergistic Effect of Pterostilbene and Acetyl Shikonin on Inhibiting Proliferation of B16F10 Cells [J]. Chinese Pharmacological Bulletin, 32(06):818-824. 7. [IF = 1.312] Qi Zhang et al."Rapid and sensitive determination of shikonin and its derivatives in the roots of Arnebia euchroma (Royle) Johnst using matrix solid-phase dispersion extraction and ultrahigh-performance liquid chromatography with photodiode array detecto 8. [IF = 2.044] Sun Qianhui et al." Ultrasound-Assisted Ionic Liquid Solid-Liquid Extraction Coupled with Aqueous Two-Phase Extraction of Naphthoquinone Pigments in Arnebia euchroma (Royle) Johnst .. "Chromatographia. 2019 Dec;82(12):1777-1789 9. [IF = 1.312] Xu Wang et al." Microwave-assisted ionic liquid microextraction combined with high performance liquid chromatography for the determination of naphthoquinones from Arnebia euchroma (Royle) Johnst."Journal Of Liquid Chromatography & Related Technologies. 20 |
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)- - Reference Information
| biological activity | Acetylshikonin, derived from purple grass root, has anti-cancer and anti-inflammatory effects. Acetylshikonin is a non-selective cytochrome P450 inhibitor with IC50 values ranging from 1.4-4.0 μM for inhibition of all P450 subtypes. Acetylshikonin is an AChE inhibitor with strong anti-apoptotic activity. |
| target | IC50: 1.4-4.0 μM (all P450s) AChE |
| use | acetyl shikonin has anti-tumor, antibacterial and anti-inflammatory effects. used for content determination/identification/pharmacological experiment, etc. |
Last Update：2024-04-09 20:52:54
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View History
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)-
yemuoside YM(12)
2,4-dichloro-8-(trifluoromethoxy)quinazoline
RS-3-Piperidinecarboxylic acid methyl ester hydrochloride
3-Piperidinylmethyl 4-chloro-2-pyridinecarboxylate hydrochloride
triton N-101
METHYL IODIDE (13C, D3)
MALONIC ACID BIS(2,4,6-TRICHLOROPHENYL) ESTER
6,7-二氯-1-乙基-4-氧代-1,4-二氢喹啉-3-甲酸
1-[1-(2-METHOXYETHYL)PIPERIDIN-4-YL]METHANAMINE
yemuoside YM(12)
2,4-dichloro-8-(trifluoromethoxy)quinazoline
RS-3-Piperidinecarboxylic acid methyl ester hydrochloride
3-Piperidinylmethyl 4-chloro-2-pyridinecarboxylate hydrochloride
triton N-101
METHYL IODIDE (13C, D3)
MALONIC ACID BIS(2,4,6-TRICHLOROPHENYL) ESTER
6,7-二氯-1-乙基-4-氧代-1,4-二氢喹啉-3-甲酸
1-[1-(2-METHOXYETHYL)PIPERIDIN-4-YL]METHANAMINE