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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 553.23 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 394.00 °F. TCC ( 201.30 °C. ) (est)
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| logP (o/w): | 2.700 (est) |
| Soluble in: |
| | water, 3.901 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for acetyl shikonin usage levels up to: | | | not for fragrance use.
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| Recommendation for acetyl shikonin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
| | [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 32464 |
| Pubchem (sid): | 134995067 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | acetic acid 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-4-methyl-pent-3-enyl ester | | 2-(1-( | acetyl oxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthalene dione | | | acetylalkannin | | | acetylshikonin | | | arnebin 3 | | | arnebin-3 | | 1-(5,8- | dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate | | 1-(5,8- | dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl acetate | | [1-(5,8- | dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate | | 1,4- | naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy- | | 1,4- | naphthalenedione, 2-[1-(acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy- | | 1,4- | naphthalenedione, 2-[1-(acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy- | | 1,4- | naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, | | | shikonin, acetyl |
Articles:
| PubMed:Acetylshikonin induces apoptosis of hepatitis B virus X protein-expressing human hepatocellular carcinoma cells via endoplasmic reticulum stress. |
| PubMed:Self-reporter shikonin-Act-loaded solid lipid nanoparticle: Formulation, physicochemical characterization and geno/cytotoxicity evaluation. |
| PubMed:Encapsulation of acetylshikonin by polyamidoamine dendrimers for preparing prominent nanoparticles. |
| PubMed:Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells. |
| PubMed:Antimicrobial and cytotoxic isohexenylnaphthazarins from Arnebia euchroma (Royle) Jonst. (Boraginaceae) callus and cell suspension culture. |
| PubMed:Effect of l-phenylalanine on PAL activity and production of naphthoquinone pigments in suspension cultures of Arnebia euchroma (Royle) Johnst. |
| PubMed:In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma. |
| PubMed:Lithospermum erythrorhizon suppresses high-fat diet-induced obesity, and acetylshikonin, a main compound of Lithospermum erythrorhizon, inhibits adipocyte differentiation. |
| PubMed:Ionization of shikonin derivatives using negative-ion electrospray mass spectrometry: [M-H]- versus [M + e]•-. |
| PubMed:Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells. |
| PubMed:The anti-proliferation effect of Aikete injection on hepatocellular carcinoma in vitro and in vivo. |
| PubMed:Callus culture of Echium italicum L. towards production of a shikonin derivative. |
| PubMed:Simultaneous densitometric determination of shikonin, acetylshikonin, and beta-acetoxyisovaleryl-shikonin in ultrasonic-assisted extracts of four Arnebia species using reversed-phase thin layer chromatography. |
| PubMed:In vitro and in vivo antitumor effects of acetylshikonin isolated from Arnebia euchroma (Royle) Johnst (Ruanzicao) cell suspension cultures. |
| PubMed:Inhibitory effect of acetylshikonin on human gastric carcinoma cell line SGC-7901 in vitro and in vivo. |
| PubMed:Identification of shikonin and its ester derivatives from the roots of Echium italicum L. |
| PubMed:The influence of acetylshikonin, a natural naphthoquinone, on the production of leukotriene B4 and thromboxane A2 in rat neutrophils. |
| PubMed:Naturally-occurring shikonin analogues--a class of necroptotic inducers that circumvent cancer drug resistance. |
| PubMed:Quantitative determination of acetylshikonin in macaque monkey blood by LC-ESI-MS/MS after precolumn derivatization with 2-mercaptoethanol and its application in pharmacokinetic study. |
| PubMed:Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in lewis lung carcinoma-bearing mice. |
| PubMed:Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues. |
| PubMed:Shikonin derivatives inhibited LPS-induced NOS in RAW 264.7 cells via downregulation of MAPK/NF-kappaB signaling. |
| PubMed:Shiunko and acetylshikonin promote reepithelialization, angiogenesis, and granulation tissue formation in wounded skin. |
| PubMed:Isolation and purification of acetylshikonin and beta-acetoxyisovalerylshikonin from cell suspension cultures of Arnebia euchroma (Royle) Johnston using rapid preparative HPLC. |
| PubMed:Simultaneous determination of naphthoquinone derivatives in Boraginaceous herbs by high-performance liquid chromatography. |
| PubMed:Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon. |
| PubMed:The shikonin derivatives and pyrrolizidine alkaloids in hairy root cultures of Lithospermum canescens (Michx.) Lehm. |
| PubMed:Evaluation of the anti-inflammatory and cytotoxic activities of naphthazarine derivatives from Onosma leptantha. |
| PubMed:Monoamine oxidase inhibitory naphthoquinones from the roots of Lithospermum erythrorhizon. |
| PubMed:The effect of acetylshikonin isolated from Lithospermum canescens roots on tumor-induced cutaneous angiogenesis. |
| PubMed:Immunomodulatory effect of shikonin derivatives isolated from Lithospermum canescens on cellular and humoral immunity in Balb/c mice. |
| PubMed:Impairment of vascular function of rat thoracic aorta in an endothelium-dependent manner by shikonin/alkannin and derivatives isolated from roots of Macrotomia euchroma. |
| PubMed:In vitro antifungal activity of naphthoquinone derivatives. |
| PubMed:Shikonin production by p-fluorophenylalanine resistant cells of Lithospermum erythrorhizon. |
| PubMed:[The anti-Candida activity of shikon]. |
| PubMed:Simultaneous analysis of shikimate-derived secondary metabolites in Lithospermum erythrorhizon cell suspension cultures by high-performance liquid chromatography. |
| PubMed:Geranylhydroquinone 3"-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures. |
| PubMed:Physical stability of shikonin derivatives from the roots of Lithospermum erythrorhizon cultivated in Korea. |
| PubMed:Enantiomeric ratio of shikonin derivatives as a possible key for the determination of the origin of lithospermi radix. |
| PubMed:Investigation of the inhibition by acetylshikonin of the respiratory burst in rat neutrophils. |
| PubMed:Impairment of phosphatidylinositol signaling in acetylshikonin-treated neutrophils. |
| PubMed:Inhibitory effect of acetylshikonin on the activation of NADPH oxidase in polymorphonuclear leukocytes in both whole cell and cell-free systems. |
| PubMed:Inhibition on platelet activation by shikonin derivatives isolated from Arnebia euchroma. |
| PubMed:Acylshikonin analogues: synthesis and inhibition of DNA topoisomerase-I. |
| PubMed:Inhibition of hind-paw edema and cutaneous vascular plasma extravasation in mice by acetylshikonin. |
| PubMed:Accelerative effect of shikonin, alkannin and acetylshikonin on the proliferation of granulation tissue in rats. |
| PubMed:Inhibition of platelet aggregation by shikonin derivatives isolated from Arnebia euchroma. |
| PubMed:[Quality of Chinese drug zicao]. |
| PubMed:[Determination of naphthoquinones in tissue cultured Zicao]. |
| PubMed:[Pharmacological studies of Shikon and Tooki. (2) Pharmacological effects of the pigment components, Shikonin and acetylshikonin]. |
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3D/inchi