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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: | 587.35 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 404.00 °F. TCC ( 206.40 °C. ) (est)
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| logP (o/w): | 3.130 (est) |
| Soluble in: |
| | water, 0.1685 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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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: |
intraperitoneal-mouse LD50 48 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 1, Pg. 60, 1980.
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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 beta,beta-dimethyl acryl shikonin usage levels up to: | | | not for fragrance use.
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| Recommendation for beta,beta-dimethyl acryl shikonin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :32465 |
| National Institute of Allergy and Infectious Diseases:Data |
| [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl]3-methylbut-2-enoate |
| Chemidplus:0024502792 |
| RTECS:EM9252400 for cas# 24502-79-2 |
References:
| | [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl]3-methylbut-2-enoate |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 32465 |
| Pubchem (sid): | 135108267 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | alkanin b,b-dimethylacrylate | | iso | arnebin I | | 2- | butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-penten-1-yl ester | | 2- | butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester | | 2- | butenoic acid, 3-methyl-, 1-(5,8-dihydro- 1,4-dihydroxy-5, 8-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester | | | crotonic acid, 3-methyl-, ester with 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone | | 1-(5,8- | dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate | | [1-(5,8- | dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl]3-methylbut-2-enoate | | beta,beta- | dimethylacrylshikonin | | | dmask | | | shikonin beta,beta-dimethyl acrylate |
Articles:
| PubMed:[Simultaneous determination of eight hydroxyl naphthoquinones in different parts of Arnebiae euchroma by HPLC]. |
| PubMed:Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp.: E. plantagineum and E. gaditanum. |
| PubMed:Development of a novel hollow-fiber liquid-phase microextraction based on oil-in-salt and its comparison with conventional one. |
| PubMed:Metabolic Profiling and Identification of Shikonins in Root Periderm of Two Invasive Echium spp. Weeds in Australia. |
| PubMed:Anti-tumor effects of shikonin derivatives on human medullary thyroid carcinoma cells. |
| PubMed:Online-storage recycling counter-current chromatography for preparative isolation of naphthaquinones from Arnebia euchroma (Royle) Johnst. |
| PubMed:Glucose uptake stimulatory potential and antidiabetic activity of the Arnebin-1 from Arnabia nobelis. |
| PubMed:Identification and localization of bioactive naphthoquinones in the roots and rhizosphere of Paterson's curse (Echium plantagineum), a noxious invader. |
| PubMed:Inhibition of c-MYC with involvement of ERK/JNK/MAPK and AKT pathways as a novel mechanism for shikonin and its derivatives in killing leukemia cells. |
| PubMed:Arnebin-1 promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway. |
| PubMed:Shikonin and its derivatives inhibit the epidermal growth factor receptor signaling and synergistically kill glioblastoma cells in combination with erlotinib. |
| PubMed:β, β-Dimethylacrylshikonin induces mitochondria-dependent apoptosis of human lung adenocarcinoma cells in vitro via p38 pathway activation. |
| PubMed:β,β-Dimethylacrylshikonin sensitizes human colon cancer cells to ionizing radiation through the upregulation of reactive oxygen species. |
| PubMed:Arnebin-1 promotes the angiogenesis of human umbilical vein endothelial cells and accelerates the wound healing process in diabetic rats. |
| PubMed:Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells. |
| PubMed:Apoptosis induced by β,β-dimethylacrylshikonin is associated with Bcl-2 and NF-κB in human breast carcinoma MCF-7 cells. |
| PubMed:Effect of β,β-dimethylacrylshikonin on inhibition of human colorectal cancer cell growth in vitro and in vivo. |
| PubMed:β,β-Dimethylacrylshikonin induces mitochondria dependent apoptosis through ERK pathway in human gastric cancer SGC-7901 cells. |
| PubMed:β,β-Dimethylacrylshikonin exerts antitumor activity via Notch-1 signaling pathway in vitro and in vivo. |
| 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:On-line continuous sampling dynamic microwave-assisted extraction coupled with high performance liquid chromatographic separation for the determination of lignans in Wuweizi and naphthoquinones in Zicao. |
| PubMed:Inhibitory effects of β,β-dimethylacrylshikonin on hepatocellular carcinoma in vitro and in vivo. |
| PubMed:Determination of the active constituents in Arnebia euchroma (Royle) Johnst. by ionic liquid-based ultrasonic-assisted extraction high-performance liquid chromatography. |
| PubMed:The anti-proliferation effect of Aikete injection on hepatocellular carcinoma in vitro and in vivo. |
| PubMed:Comparative study on enantiomeric excess of main akannin/shikonin derivatives isolated from the roots of three endemic Boraginaceae plants in China. |
| PubMed:[Simultaneous determination of five active components in compound preparation of Dangguishuan by high-performance liquid chromatography]. |
| PubMed:Identification of shikonin and its ester derivatives from the roots of Echium italicum L. |
| PubMed:Quantitative determination of beta,beta-dimethylacrylshikonin (DASK) in rat whole blood by liquid chromatography-tandem mass spectrometry with pre-column derivation and its pharmacokinetic application. |
| PubMed:Naturally-occurring shikonin analogues--a class of necroptotic inducers that circumvent cancer drug resistance. |
| PubMed:Shikonin derivatives inhibited LPS-induced NOS in RAW 264.7 cells via downregulation of MAPK/NF-kappaB signaling. |
| PubMed:Simultaneous determination of naphthoquinone derivatives in Boraginaceous herbs by high-performance liquid chromatography. |
| PubMed:Evaluation of the anti-inflammatory and cytotoxic activities of naphthazarine derivatives from Onosma leptantha. |
| 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:Shikonin production by p-fluorophenylalanine resistant cells of Lithospermum erythrorhizon. |
| PubMed:Arnebin-1 accelerates normal and hydrocortisone-induced impaired wound healing. |
| PubMed:Accelerative effect of "nanshikon" and its constituents on the proliferation of granulation tissue in rats. |
| PubMed:Inhibition on platelet activation by shikonin derivatives isolated from Arnebia euchroma. |
| PubMed:Inhibition of platelet aggregation by shikonin derivatives isolated from Arnebia euchroma. |
| PubMed:[Determination of naphthoquinones in tissue cultured Zicao]. |
| PubMed:Comparative in vitro and in vivo effect of lactones and arnebins on Trichophyton mentagrophytes and Candida albicans. |
| PubMed:[Anti-inflammatory effect of beta, beta-dimethylacrylshikonin (author's transl)]. |
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3D/inchi