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
Identification
| Name | beta-hydroxyisovaleryl shikonin |
| CAS Number | 7415-78-3 |
| FDA UNII | Search |
| Molecular Formula | C21 H24 O7 |
| Molecular Weight | 388.41668000 |
Regulatory
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) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| 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-hydroxyisovaleryl shikonin usage levels up to | not for fragrance use. |
| Recommendation for beta-hydroxyisovaleryl shikonin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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
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.