시코닌
시코닌 · Isoarnebin 4 · gromwell red · SHIKONIN · Shikonine · c.i.75535 · NSC 252844 · Shikonin-RM
식별자 및 물리적 특성
| CAS No. | 517-89-5 |
|---|---|
| 분자식 | C16H16O5 |
| 평균 분자량 | 288.29 g/mol |
| 단동위원소 질량 | 288.09977361 g/mol |
| SMILES | CC(C)=CC[C@@H](O)C1=CC(=O)c2c(O)ccc(O)c2C1=O |
| InChIKey | NEZONWMXZKDMKF-SNVBAGLBSA-N |
| PubChem CID | 479503 |
| ChEMBL | CHEMBL9470 |
| ChEBI | CHEBI:81068 |
| EC No. | 610-730-7 |
| DTXSID | DTXSID30199653 |
| 현지명 | 시코닌 |
화학 및 물리적 성질
| XLogP | 3 |
|---|---|
| 극성 표면적 | 94.8 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 21 |
| 형식 전하 | 0 |
| 복잡도 | 501 |
| 밀도 | 1.373 g/cu cm1.373±0.06 g/cm3(Predicted) |
| Color/Form | White or slightly yellow crystalline powder |
| 용해도 | Practically insoluble in aqueous solutionsDMSO : ≥ 31 mg/mL (107.53 mM) |
| 녹는점 | 147 °C148℃ |
| 끓는 점 | 567.4±50.0 °C(Predicted) |
| 저장 조건 | -20°C |
| pKa(산도 계수) | 7.34±0.20(Predicted) |
| 물리적 상태 | 적색 결정성 고체. |
| 색상 | 갈색 |
| 헨리 상수 | 1.2×109 mol/(m3Pa) at 25℃, HSDB (2015) |
| 주요 응용 | 음식 및 음료 |
| 화장품 원료 기능 | 색소피부 컨디셔닝 - 기타 |
| InChI | InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1 |
| InChIKey | NEZONWMXZKDMKF-SNVBAGLBSA-N |
| SMILES | C1(=O)C2=C(C(O)=CC=C2O)C(=O)C=C1[C@H](O)C/C=C(\C)/C |
| LogP(분배 계수) | 4.350 (est) |
화학적 성질
Purple-brown crystals with a needle-like shape, melting at 147 ° C, with a rotativity of αD20 = +135 ° (in benzene). It dissolves readily in phenethyl ether, acetone, chloroform, methanol, ethanol, glycerol, animal and vegetable oils, and alkaline aqueous solutions, but is insoluble in water. Its color changes depending on the pH value: at pH 4-6, it turns red; at pH 8, it becomes purple; and at pH 10-12, it appears blue. It exhibits excellent resistance to light, heat, and oxidation, but is reactive to reducing agents, causing the formation of dark purple when exposed to iron ions. Additionally, Shikonin has certain antibacterial effect.
안전 및 규제
| GHS 분류 | WarningH302+H312+H332 (50%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]H412 (50%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 화재 가능성 | Not flammable or combustible. |
| Toxic Combustion Products | Hazardous decomposition products formed under fire conditions. Carbon oxides. |
| Hazard Classes and Categories | Aquatic Chronic 3 (50%) |
| 소화 절차 | Extinguishing Media: Carbon dioxide, dry chemical powder, polymer foam, water spray.Special Firefighting Procedures: Use self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes. |
| 보관 조건 | Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2-8 °C. Store with desiccant.... Store at room temperature. It should be kept in a tightly closed container. |
| 정리 방법 | For spill clean up, wear suitable protective clothing, chemical resistant rubber gloves, rubber boots, and chemical safety goggles. Self contained breathing apparatus or NIOSH/MSHA approved respirator is required.... Wipe up spill and place in sealed container and hold for disposal. Avoid raising dust. Ventilate the area and wash spill site after material has been removed. |
| 처리 방법 | SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
용도
개요
Shikonin could be found in the plant of Lithospermum erythrorhizon Sieb. et. Zucc and Arnebia euchroma (Royle) Johnst. It could also be produced using plant cell culture techniques. Shikonin is recorded in British Pharmacopoeia as a reference compound. Zicao, a traditional Chinese medicine firstly recorded in Shen Nong’s Herbal Classic, has long been used medically in history . Chinese Pharmacopoeia (Edition 2015) recorded the root of Arnebia euchroma (Royle) Johnst and Arnebia guttata Bge as Zicao, which is mainly used for inflammatory diseases such as macular eruptions, measles, sore throat, carbuncles, and burns.
역사
Kuroda and Majima firstly identified acetyl shikonin from L. erythrorhizon in 1922 , followed by the discovery of other shikonin derivatives, including shikonin. The chemical structure of shikonin was not precisely identified till 1936 for its high physicochemical similarity with naphthazarin . There have been about 500 publications on shikonin up to now. Great attention has also been paid on the biosynthesis of shikonin and its derivatives, and an increasing number of shikonin derivatives have been designed and synthesized for exploring their antitumor effect. There are two types of derivatives: one is modifications of 1′-OH with parent nucleus naphthazarin remained and the other is modifications of both 1′-OH and parent nucleus naphthazarin, as shown in Fig. 3c, d .
용도
Shikonin has been used as a red dye for centuries and is reported to possess medicinal properties such as antibacterial, anti-inflammatory and antitumor activities. It occurs as an acetyl derivative in the Japanese shikone, Lithospermum erythrorhizon, another member of the Boraginaceae family. It is the (R)-optical isomer of alkannin. Tissue cultures of L. erythrorhizon are used in Japan to manufacture shikonin mainly for cosmetic use. Both alkannin and shikonin are mordant dyes producing violet to gray colors on fabrics. In Japan, shikonin was used to dye fabrics a color known as Tokyo Violet. Shikalkin the racemate, has been synthesized.
일반 설명
Shikonin is a naturally occurring naphthoquinine isolated from the dried root of L. erythrorhizon, an herb used in traditional Chinese medicine. It increases glucose uptake by adipocytes and myocytes and inhibits the activity of phosphatase and tensin homolog (PTEN; IC50 = 2.7 μM). It inhibits glycolysis in cancer cells by inhibiting tumor-specific pyruvate kinase M2 (IC50 = 0.3 μM). Shikonin induces cell death consistent with necroptosis in MCF-7 and HEK293 cancer cell lines. It inhibits leukocyte migration, downregulates chemokine receptor expression, and inhibits HIV-1 replication at nanomolar concentrations. Shikonin exhibits anti-inflammatory activity, reducing joint swelling and cartilage destruction in a mouse model of collagen-induced arthritis.