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C5624

Sigma-Aldrich

Cryptotanshinone

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C19H20O3
CAS Number:
35825-57-1
Molecular Weight:
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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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