acetyl shikonin
[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
Identification
| Name | acetyl shikonin |
| IUPAC | [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate |
| CAS Number | 54984-93-9 |
| FDA UNII | Search |
| Molecular Formula | C18 H18 O6 |
| Molecular Weight | 330.33666000 |
| Nikkaji Number | J1.354.872B |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 553.23 °C. @ 760.00 mm Hg (est) |
| Flash Point | 394.00 °F. TCC ( 201.30 °C. ) (est) |
| logP (o/w) | 2.700 (est) |
| Soluble in | water, 3.901 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for acetyl shikonin usage levels up to | not for fragrance use. |
| Recommendation for acetyl shikonin flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
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
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]â¢-.
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].