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beta-hydroxyisovaleryl shikonin
1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate

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CAS Number: 7415-78-3Picture of molecule3D/inchi
Other(deleted CASRN):87585-33-9
FDA UNII: Search
XlogP3-AA:3.40 (est)
Molecular Weight:388.41668000
Formula:C21 H24 O7
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 616.91 °C. @ 760.00 mm Hg (est)
Flash Point: 420.00 °F. TCC ( 215.80 °C. ) (est)
logP (o/w): 2.424 (est)
Soluble in:
 water, 6.859 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
beta-HYDROXYISOVALERYLSHIKONIN 95%
Nacalai USA
For experimental / research use only.
b-Hydroxyisovalerylshikonin
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for beta-hydroxyisovaleryl shikonin usage levels up to:
 not for fragrance use.
 
Recommendation for beta-hydroxyisovaleryl shikonin flavor usage levels up to:
 not for flavor use.
 
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 :100203
National Institute of Allergy and Infectious Diseases:Data
[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl]3-hydroxy-3-methylbutanoate
Chemidplus:0087798741
 
References:
 [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl]3-hydroxy-3-methylbutanoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):100203
Pubchem (sid):135057619
 
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
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 gromwell purple gromwell
Search Trop Picture
 
Synonyms:
 alkannin-b-hydroxyisovalerate
 alkannin-beta-hydroxyisovalerate
 butanoic acid, 3-hydroxy-3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-penten-1-yl ester
1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate
[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl]3-hydroxy-3-methylbutanoate
beta-hydroxyisovalerylshikonin
 

Articles:

PubMed:Anti-inflammatory effects of β-hydroxyisovalerylshikonin in BV2 microglia are mediated through suppression of the PI3K/Akt/NF-kB pathway and activation of the Nrf2/HO-1 pathway.
PubMed:Retraction notice to "β-Hydroxyisovalerylshikonin has a profound anti- growth activity in human endometrial and ovarian cancer cells" [Gynecol. Oncol. 109 (2008) 107-114].
PubMed:In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma.
PubMed:Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
PubMed:Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues.
PubMed:Anti-neoplastic effect of β-hydroxyisovalerylshikonin on a human choriocarcinoma cell line.
PubMed:Mechanism of inhibition of tumor angiogenesis by beta-hydroxyisovalerylshikonin.
PubMed:Beta-hydroxyisovalerylshikonin has a profound anti-growth activity in human endometrial and ovarian cancer cells.
PubMed:A tyrosine kinase inhibitor, beta-hydroxyisovalerylshikonin, induced apoptosis in human lung cancer DMS114 cells through reduction of dUTP nucleotidohydrolase activity.
PubMed:Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon.
PubMed:Beta-hydroxyisovalerylshikonin induces apoptosis and G0/G1 cell-cycle arrest of endometriotic stromal cells: a preliminary in vitro study.
PubMed:Involvement of tumor necrosis factor receptor-associated protein 1 (TRAP1) in apoptosis induced by beta-hydroxyisovalerylshikonin.
PubMed:[Basic studies for the development of anticancer, antidementia, and taste modifier drugs].
PubMed:Beta-hydroxyisovalerylshikonin and cisplatin act synergistically to inhibit growth and to induce apoptosis of human lung cancer DMS114 cells via a tyrosine kinase-dependent pathway.
PubMed:A shikonin derivative, beta-hydroxyisovalerylshikonin, is an ATP-non-competitive inhibitor of protein tyrosine kinases.
PubMed:Beta-hydroxyisovalerylshikonin is a novel and potent inhibitor of protein tyrosine kinases.
PubMed:Beta-hydroxyisovalerylshikonin induces apoptosis in human leukemia cells by inhibiting the activity of a polo-like kinase 1 (PLK1).
PubMed:Synergistic inhibitory effects of transplatin and beta-hydroxyisovalerylshikon on carcinoma A431 cells involve epidermal growth factor receptor.
PubMed:Shikonin production by p-fluorophenylalanine resistant cells of Lithospermum erythrorhizon.
PubMed:Physical stability of shikonin derivatives from the roots of Lithospermum erythrorhizon cultivated in Korea.
PubMed:beta-hydroxyisovalerylshikonin inhibits the cell growth of various cancer cell lines and induces apoptosis in leukemia HL-60 cells through a mechanism different from those of Fas and etoposide.
 
Notes:
None found
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