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 |
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. |
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. |
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 |
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. |