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C5624

Sigma-Aldrich

Cryptotanshinone

≥98% (HPLC)

Sinónimos:

1,2,6,7,8,9-hexahydro-1,6,6-trimethyl- (R)-phenanthro(1,2-b)furan-10,11-dione, Cryptotanshinon, Tanshinone c

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About This Item

Fórmula empírica (notación de Hill):
C19H20O3
Número de CAS:
35825-57-1
Peso molecular:
296.36
MDL number:
MFCD07636810
UNSPSC Code:
12352200
PubChem Substance ID:
329775097
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -80 to -99°, c = 0.5 in chloroform-d

storage condition

desiccated
protect from light

color

orange-brown

solubility

DMSO: ≥5 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

C[C@H]1COC2=C1C(=O)C(=O)c3c4CCCC(C)(C)c4ccc23

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

InChI key

GVKKJJOMQCNPGB-JTQLQIEISA-N

Biochem/physiol Actions

Cryptotanshinone is a quinoid diterpene isolated from the root of the Asian medicinal plant, Salvia miotiorrhiza bunge. Recently it was discovered that the compound is a potent STAT3 inhibitor. Cryptotanshinone rapidly inhibited STAT3 Tyr705 phosphorylation through a JAK2-independent mechanism. Cryptotanshinone selectively inhibits STAT3-activated cell lines through binding to monomer STAT3, subsequently blocking the dimerization and inhibiting STAT3 transcriptional regulatory activity. Previously, it was reported that the compound counteracts inflammation through the inhibition of cyclooxygenase II activity and endothelin-1 expression. In traditional oriental medicine dried roots of Salvia Miltiorrhiza Bunge (Danshen) have commonly been used for the treatment of circulatory disorders, liver disease, coronary heart disease, hepatitis, and chronic renal failure.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Jia-Hau Yen et al.
Molecular therapy oncolytics, 26, 158-174 (2022-07-22)
Dampening tumor growth by converting tumor-associated macrophages (TAMs) from M2/repair-types to M1/kill-types is of high interest. Here, we show that cryptotanshinone (CPT) can function as an antitumor immune modulator that switches TAMs from an M2 to an M1 phenotype, leading
Yongpeng Zhang et al.
Drug development research, 82(4), 581-588 (2020-12-20)
Coronary microembolization (CME) is a prevalent cardiovascular disease, especially nowadays when percutaneous coronary intervention is widely applied. However, neither cardio-protective agents nor devices for distal protection could effectively prevent the occurrence of CME. Therefore, we aimed to develop a new
Zhiyuan Lu et al.
Molecular biology reports, 51(1), 436-436 (2024-03-23)
Elevated levels of adipokine chemerin have been identified in oral squamous cell carcinoma (OSCC) and found to be associated with metastasis to the cervical lymph nodes. The underlying mechanism through which chemerin affects OSCC progression is unclear. The aims of
Chunlong Ma et al.
ACS pharmacology & translational science, 5(2), 102-109 (2022-02-19)
SARS-CoV-2 encodes two viral cysteine proteases, the main protease (Mpro) and the papain-like protease (PLpro), both of which are validated antiviral drug targets. PLpro is involved in the cleavage of viral polyproteins as well as immune modulation by removing ubiquitin
Yan Luo et al.
Cancer prevention research (Philadelphia, Pa.), 4(12), 2083-2091 (2011-09-02)
Cryptotanshinone (CPT), isolated from the plant Salvia miltiorrhiza Bunge, is a potential anticancer agent. However, the underlying mechanism remains to be defined. Here, we show that CPT inhibited lymphangiogenesis in an in vitro model (tube formation). This effect was partly
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