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D0947

Sigma-Aldrich

Dihydrotanshinone I

≥98% (HPLC)

Synonym(s):

Dihydrotanshinone I, (-)-Dihydrotanshinone I, 15,16-Dihydrotanshinone I

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About This Item

Empirical Formula (Hill Notation):
C18H14O3
CAS Number:
87205-99-0
Molecular Weight:
278.30
MDL number:
MFCD28016070
UNSPSC Code:
12352200
PubChem Substance ID:
329798655
NACRES:
NA.25

biological source

Salvia miltiorrhiza

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

red

solubility

ethanol: 1 mg/mL, clear, orange to red

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

C[C@H]1COC(C2=C3C4=C(C=C2)C(C)=CC=C4)=C1C(C3=O)=O

InChI

1S/C18H14O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h3-7,10H,8H2,1-2H3/t10-/m0/s1

InChI key

HARGZZNYNSYSGJ-JTQLQIEISA-N

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General description

DihydrotanshinoneI (DHTS) is a tanshinone derivative which is a soluble diterpene quinone pigment of danshen.

Application

Dihydrotanshinone I (DHTS) has been used:
  • to study its cytocidal effects on chemosensitive ovarian cancer cells with or without platinum-based chemotherapy
  • as a treatment to study its inhibitory effects on triple-negative breast cancer cells growth by modulating epithelial-mesenchymal transition (EMT) markers
  • as a potential SARS-CoV-2 papain-like protease (PLpro) inhibitor
  • as a human antigen R (HuR) inhibitor to study its role in Th17 cell differentiation related to autoimmune neuroinflammation
  • as a reference standard to analyze Salvia miltiorrhiza Bunge extract (SME) components using high-performance liquid chromatography(HPLC)

Biochem/physiol Actions

Dihydrotanshinone Iis a potent anti-cancer agent with its cytotoxic, apoptosis, cell cycle arresteffects and inhibition of angiogenesis, and metastasis in cancer cells. Italso exerts cardiovascular and cerebrovascular protective effects. DHTS isan anti-inflammatory, anti-ischemia-reperfusion (I/R), anti-allergic,anti-Alzheimer’s disease properties. It is also effective againstdrug-resistant cancer cells.
Tanshinone extracted from a herb, Salvia miltiorrhiza, commonly used in Chinese traditional medicine. A significant decrease in tumor growth was observed using dihydrotanshinone I and irradiation treatment with mouse xenograft model.

Storage Class Code

11 - 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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Daifei Wang et al.
Biopharmaceutics & drug disposition, 41(1-2), 54-63 (2020-01-17)
Salvia miltiorrhiza is one of the most commonly used traditional Chinese medicines in the treatment of cardiovascular and cerebrovascular diseases. Cryptotanshinone (CTS), tanshinone IIA (Tan IIA), dihydrotanshinone I (diTan I), and tanshinone I (Tan I) are the main active compounds
15,16-Dihydrotanshinone I, a Compound of Salvia miltiorrhiza Bunge, Induces Apoptosis through Inducing Endoplasmic Reticular Stress in Human Prostate Carcinoma Cells.
Chuang MT, Ho FM, Wu CC, Zhuang SY, Lin SY, Suk FM, Liang YC.
Evidence-Based Complementary and Alternative Medicine : ECAM, 2011 (2011)
Jing Chen et al.
Journal of immunology (Baltimore, Md. : 1950), 204(8), 2076-2087 (2020-03-15)
Dysregulated Th17 cell differentiation is associated with autoimmune diseases such as multiple sclerosis, which has no curative treatment. Understanding the molecular mechanisms of regulating Th17 cell differentiation will help find a novel therapeutic target for treating Th17 cell-mediated diseases. In
Preet Lal et al.
Nucleic acids research, 45(16), 9514-9527 (2017-09-22)
The Human antigen R protein (HuR) is an RNA-binding protein that recognizes U/AU-rich elements in diverse RNAs through two RNA-recognition motifs, RRM1 and RRM2, and post-transcriptionally regulates the fate of target RNAs. The natural product dihydrotanshinone-I (DHTS) prevents the association
Danshen extract 15,16-dihydrotanshinone I functions as a potential modulator against metabolic syndrome through multi-targeted pathways.
Liu Q, Zhang Y, Lin Z, Shen H, Chen L, Hu L, Jiang H, Shen X.
The Journal of Steroid Biochemistry and Molecular Biology, 4-5, 155-163 (2010)
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