ChemicalBook CAS DataBase List 35825-57-1

35825-57-1

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
Molecular Formula	C19H22O3
MDL Number	MFCD00210488
Molecular Weight	298.38
MOL File	35825-57-1.mol

Chemical Properties

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 Rotation	[α]/D -85.0±3.0°, c = 0.1 in chloroform
λmax	263nm(lit.)
BRN	5445400
Major Application	food and beverages
InChI	InChI=1S/C19H20O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,10H,4-5,8-9H2,1-3H3/t10-/m0/s1
InChIKey	IJSBKZLSTIFYIE-FPKDZHNTSA-N
SMILES	O1C[C@H](C)C2C(=O)C(=O)C3=C(C1=2)C=CC1=C3CCCC1(C)C
LogP	4.130 (est)
CAS DataBase Reference	35825-57-1(CAS DataBase Reference)

Safety Data

Hazard Codes	T,N
Risk Statements	25-50/53 less more
Safety Statements	45-60-61 less more
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
Storage Class	13 - Non Combustible Solids

Hazard Information

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

Supplier

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