beta,beta-dimethyl acryl shikonin
shikonin beta,beta-dimethyl acrylate
 
Notes:
None found
  • BOC Sciences
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      Product(s):
      24502-79-2 beta,beta-Dimethylacrylshikonin >98%
      Dimethylacrylshikonin usually can be found in the roots of Lithosperraum erythrorhizon Sieb. et Zucc. Injection of Dimethylacrylshikonin combined with IR treatment significantly suppressed tumor growth of the HCT-116 xenograft.
       
       
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      Product(s):
      D2118 (β,β-Dimethylacryl)shikonin >90.0%(HPLC)
       
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CAS Number: 24502-79-2Picture of molecule3D/inchi
Nikkaji Web: J256.532C
MDL: MFCD00143687
XlogP3-AA: 5.00 (est)
Molecular Weight: 370.40154000
Formula: C21 H22 O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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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:
Alfa Biotechnology
For experimental / research use only.
beta,beta-Dimethylacrylshikonin 98%
BOC Sciences
For experimental / research use only.
beta,beta-Dimethylacrylshikonin >98%
Odor: characteristic
Use: Dimethylacrylshikonin usually can be found in the roots of Lithosperraum erythrorhizon Sieb. et Zucc. Injection of Dimethylacrylshikonin combined with IR treatment significantly suppressed tumor growth of the HCT-116 xenograft.
Carbosynth
For experimental / research use only.
beta,beta-Dimethylacrylshikonin
Coompo
For experimental / research use only.
Dimethylacrylshikonin from Plants ≥98%
Matrix Scientific
For experimental / research use only.
beta,beta-Dimethylacrylshikonin, 95+%
Nacalai USA
For experimental / research use only.
b,b-Dimethylacrylshikonin
Santa Cruz Biotechnology
For experimental / research use only.
(β,β-Dimethylacryl)shikonin
TCI AMERICA
For experimental / research use only.
(β,β-Dimethylacryl)shikonin >90.0%(HPLC)
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Safety Information:
Preferred SDS: View
 
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:
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.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
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.
 
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
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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
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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
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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
CHEMBL: View
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Export Tariff Code: 2914.50.3000
VCF-Online: VCF Volatile Compounds in Food
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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
 gromwell purple gromwell
Search Trop  Picture
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Synonyms:
 alkanin b,b-dimethylacrylate
isoarnebin 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
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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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