beta,beta-dimethyl acryl shikonin
shikonin beta,beta-dimethyl acrylate
Identification
| Name | beta,beta-dimethyl acryl shikonin |
| IUPAC | [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl]3-methylbut-2-enoate |
| CAS Number | 24502-79-2 |
| FDA UNII | Search |
| Molecular Formula | C21 H22 O6 |
| Molecular Weight | 370.40154000 |
| MDL Number | MFCD00143687 |
| Nikkaji Number | J256.532C |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 587.35 °C. @ 760.00 mm Hg (est) |
| Flash Point | 404.00 °F. TCC ( 206.40 °C. ) (est) |
| logP (o/w) | 3.130 (est) |
| Soluble in | water, 0.1685 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 48 mg/kg |
| 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 beta,beta-dimethyl acryl shikonin usage levels up to | not for fragrance use. |
| Recommendation for beta,beta-dimethyl acryl shikonin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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
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]â¢-.
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)].