beta,beta-dimethyl acryl shikonin

shikonin beta,beta-dimethyl acrylate

CAS: 24502-79-2 C21 H22 O6 MW: 370.40154000

Identification

Namebeta,beta-dimethyl acryl shikonin
IUPAC[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl]3-methylbut-2-enoate
CAS Number24502-79-2
FDA UNIISearch
Molecular FormulaC21 H22 O6
Molecular Weight370.40154000
MDL NumberMFCD00143687
Nikkaji NumberJ256.532C

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 SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 48 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for beta,beta-dimethyl acryl shikonin usage levels up tonot for fragrance use.
Recommendation for beta,beta-dimethyl acryl shikonin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

gromwell purple gromwell

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]•-. 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)].