acetyl shikonin
[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
 
Notes:
from roots of boraginacea.
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CAS Number: 54984-93-9Picture of molecule3D/inchi
Other: 106295-33-4
Nikkaji Web: J1.354.872B
XlogP3-AA: 3.50 (est)
Molecular Weight: 330.33666000
Formula: C18 H18 O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Coompo
For experimental / research use only.
Acetylshikonin from Plants ≥98%
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
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.
 
Recommendation for acetyl shikonin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 32464
National Institute of Allergy and Infectious Diseases: Data
 [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
Chemidplus: 0054984939
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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
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
KEGG (GenomeNet): C17413
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 arnebia euchroma root
Search Trop  Picture
 gromwell purple gromwell root
Search Trop  Picture
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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
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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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