| Identification | More | [Name]
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione | [CAS]
35825-57-1 | [Synonyms]
CRYPTOTANSHINONE
(r)-1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione
TANSHINONE, CRYPTO
98% BY HPLC
CRYPTOTANSHINONE >
TANSHINONE, CRYPTO(P)
hexahydro-1,6,6-trimethyl-,(R)-
Phenanthro[1,2-b]furan-10,11-dione,1,2,6,7,8,9- | [Molecular Formula]
C19H22O3 | [MDL Number]
MFCD00210488 | [Molecular Weight]
298.38 | [MOL File]
35825-57-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
192°C(lit.) | [Boiling point ]
459.0±45.0 °C(Predicted) | [density ]
1.23±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: ≥5mg/mL | [form ]
powder | [color ]
orange-brown | [optical activity]
[α]/D -85.0±3.0°, c = 0.1 in chloroform | [λmax]
263nm(lit.) | [BRN ]
5445400 | [InChIKey]
IJSBKZLSTIFYIE-FPKDZHNTSA-N | [LogP]
4.130 (est) | [CAS DataBase Reference]
35825-57-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N | [Risk Statements ]
25-50/53 | [Safety Statements ]
45-60-61 | [RIDADR ]
UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all | [WGK Germany ]
3 | [RTECS ]
SF8282645 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29321900 |
| Hazard Information | Back Directory | [Chemical Properties]
Orange powder | [Uses]
inhibits angiogenesis | [Definition]
ChEBI: Cryptotanshinone is an abietane diterpenoid. It has a role as an anticoronaviral agent. | [General Description]
Cryptotanshinone, a cell-permeable diterpene quinone and naturally occurring herbal constituent of Salvia miltiorrhiza Bunge (Danshen), is shown to inhibit the constitutive STAT3 Tyr705 phosphorylation in DU145 prostate cancer cells (>90% inhibition in 1 h at 7 μM) independent of the IL-6/JAK/STAT3 signaling pathway, resulting in a blockage of STAT3 dimerization, nuclear translocation, and STAT3-dependent transcription activity (by ~80% in 24 h at 7 μM). Cryptotanshinone is also reported to deplete cellular ATP level (by 75% in 12 h at 20 μM in C2C12 myotubes), resulting in an indirect activation of cellular AMPK pathways and an enhancement of insulin-stimulated cellular glucose uptake in C2C12 myotubes and 3T3-L1 adipocytes (by ~1.3- and 1.9-fold, respectively). Cryptotanshinone is demonstrated to be an orally active hypoglycemic agent in ob/ob mice, db/db mice, and ZDF rats in vivo (600 mg/kg/day). | [Biological Activity]
Major tanshinone isolated from Salvia miltiorrhiza that exhibits multiple activities. Exhibits antitumor activity via inhibition STAT3 activity (IC 50 = 4.6 μ ). Displays antibacterial and anti-inflammatory activity and acts as an antidiabetes and antiobesity agent via activation of AMP-activated protein kinase (AMPK). Also improves cognitive impairment in Alzheimer's disease transgenic mice by inhibition of acetylcholinesterase (IC 50 = 4.09 μ ) and reduction in A β peptide generation. | [Biochem/physiol Actions]
Cryptotanshinone is an antibacterial and anti-inflammatory compound originally extracted from the roots of Salvia miltiorrhiaz (danshen). Cryptotanshinone has been found to inhibit HIF activation and to inhibit macrophage migration negatively regulate the PI3K pathway. It has demonstrated activity against several strains of Staphylococcus aureus. | [Cytotoxicity]
IC50 (μg/mL): 1.27 (A549), 1.39 (TOV-21G) (Chang et al. 2013) | [storage]
Room temperature |
| Spectrum Detail | Back Directory | [Spectrum Detail]
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione(35825-57-1)MS
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione(35825-57-1)IR1
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione(35825-57-1)IR2
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