EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

cryptotanshinone
(R)-1,6,6-trimethyl-1,2,6,7,8,9-hexahydro-phenanthro[1,2-b]furan-10,11-dione

Supplier Sponsors

CAS Number: 35825-57-1Picture of molecule3D/inchi
FDA UNII: 5E9SXT166N
Nikkaji Web:J865.486G
MDL:MFCD07636810
XlogP3-AA:3.80 (est)
Molecular Weight:296.36600000
Formula:C19 H20 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:red-brown powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 459.03 °C. @ 760.00 mm Hg (est)
Flash Point: 398.00 °F. TCC ( 203.40 °C. ) (est)
logP (o/w): 4.130 (est)
Soluble in:
 water, 0.5213 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Cryptotanshinone 98%
BOC Sciences
For experimental / research use only.
Cryptotanshinone
Odor: characteristic
Use: Cryptotanshinone, a natural cell-permeable diterpene quinone isolated from Salvia miltiorrhiza, it inhibits acetylcholinesterase (IC50 = 4.09 mM) and reduces A peptide generation so that can treat Alzheimer's disease. It also inhibits STAT3 activity (IC Implicated in Alzheimer's disease
Carbosynth
For experimental / research use only.
Cryptotanshinone
Coompo
For experimental / research use only.
Cryptotanshinone from Plants ≥96%
Odor: characteristic
Use: Cryptotanshinone could have diverse effects on cell cycle events in melanoma cell lines with different metastatic capacity. This property might offer an opportunity to study underlying mechanisms for the different antitumor effects of administered Cryptotanshinone in B16 and B16BL6 cells. Cryptotanshinone, the major active constituent isolated from the root of Salvia miltiorrhiza Bunge, has been recently evaluated for its anti-cancer activity, but the molecular mechanisms underlying these activities remain poorly understood. In particular, it remains completely unknown as to whether or not cryptotanshinone can induce endoplasmic reticulum (ER) stress. Herein, we identify cryptotanshinone as a potent stimulator of ER stress, leading to apoptosis in many cancer cell lines, including HepG2 hepatoma and MCF7 breast carcinoma, and also demonstrate that mitogen-activated protein kinases function as mediators in this process. Reactive oxygen species generated by cryptotanshinone have been shown to play a critical role in ER stress-induced apoptosis. Cryptotanshinone also evidenced sensitizing effects to a broad range of anti-cancer agents including Fas/Apo-1, TNF-a, cisplatin, etoposide or 5-FU through inducing ER stress, highlighting the therapeutic potential in the treatment of human hepatoma and breast cancer. 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 (IC50 = 4.09 µM) and reduction in Aβ peptide generation.
Jiangyin Healthway
Cryptotanshinone
New functional food ingredients
Santa Cruz Biotechnology
For experimental / research use only.
Cryptotanshinone
Sigma-Aldrich: Sigma
For experimental / research use only.
Cryptotanshinone ≥98% (HPLC)
sds
TCI AMERICA
For experimental / research use only.
Cryptotanshinone >97.0%(HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for cryptotanshinone usage levels up to:
 not for fragrance use.
 
Recommendation for cryptotanshinone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :160254
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(1R)-1,6,6-trimethyl-2,7,8,9-tetrahydro-1H-naphtho[1,2-g][1]benzofuran-10,11-dione
Chemidplus:0035825571
 
References:
 (1R)-1,6,6-trimethyl-2,7,8,9-tetrahydro-1H-naphtho[1,2-g][1]benzofuran-10,11-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):160254
Pubchem (sid):135115662
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB35220
FooDB:FDB013869
Export Tariff Code:2932.99.6100
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 rosemary
Search Trop Picture
 sage red sage
Search Trop Picture
 
Synonyms:
(-)-cryptotanshinone
(R)-1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione
 phenanthro(1,2-b)furan-10,11-dione, 1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-, (R)-
 phenanthro[1,2-b]furan-10,11-dione, 1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-, (1R)-
 tanshinone C
(R)-1,6,6-trimethyl-1,2,6,7,8,9-hexahydro-phenanthro[1,2-b]furan-10,11-dione
(1R)-1,6,6-trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dione
(R)-1,6,6-trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dione
(1R)-1,6,6-trimethyl-2,7,8,9-tetrahydro-1H-naphtho[1,2-g][1]benzofuran-10,11-dione
 

Articles:

PubMed:Cryptotanshinone Reverses Reproductive and Metabolic Disturbances in PCOS Model Rats via Regulating the Expression of CYP17 and AR.
PubMed:[Effects on Salvia miltiorrhiza hairy roots of tanshinones content accumulation after treated with fosmidomycin].
PubMed:[Influence of continuous cropping years on yield and active compounds in Salvia miltiorrhiza f. alba].
PubMed:Synergistic Effect between Cryptotanshinone and Antibiotics against Clinic Methicillin and Vancomycin-Resistant Staphylococcus aureus.
PubMed:Cryptotanshinone Induces Inhibition of Breast Tumor Growth by Cytotoxic CD4+ T Cells through the JAK2/STAT4/ Perforin Pathway.
PubMed:Inhibitory effect of cryptotanshinone on angiogenesis and Wnt/β-catenin signaling pathway in human umbilical vein endothelial cells.
PubMed:Effects of Streptomyces pactum Act12 on Salvia miltiorrhiza Hairy Root Growth and Tanshinone Synthesis and Its Mechanisms.
PubMed:Tissue-smashing based ultra-rapid extraction of chemical constituents in herbal medicines.
PubMed:Cryptotanshinone inhibits lung tumorigenesis and induces apoptosis in cancer cells in vitro and in vivo.
PubMed:Cryptotanshinone attenuates cardiac fibrosis via downregulation of COX-2, NOX-2 and NOX-4.
PubMed:Syntheses of diacyltanshinol derivatives and their suppressive effects on macrophage foam cell formation by reducing oxidized LDL uptake.
PubMed:The Nrf2-inducers tanshinone I and dihydrotanshinone protect human skin cells and reconstructed human skin against solar simulated UV.
PubMed:Opposite Effects of Single-Dose and Multidose Administration of the Ethanol Extract of Danshen on CYP3A in Healthy Volunteers.
PubMed:Cryptotanshinone induces G1 cell cycle arrest and autophagic cell death by activating the AMP-activated protein kinase signal pathway in HepG2 hepatoma.
PubMed:Protective effect of cryptotanshinone on lipopolysaccharide-induced acute lung injury in mice.
PubMed:RNA interference-mediated repression of SmCPS (copalyldiphosphate synthase) expression in hairy roots of Salvia miltiorrhiza causes a decrease of tanshinones and sheds light on the functional role of SmCPS.
PubMed:[Investigation on equilibrium solubility and apparent oil/water partition coefficient of diterpenoid tanshinone component by similarity analysis methods].
PubMed:A Simple and Reliable Method for Distinguishing Danshen in Salvia: Simultaneous Quantification of Six Active Compositions by HPLC.
PubMed:Hepatoprotective effect of cryptotanshinone from Salvia miltiorrhiza in D-galactosamine/lipopolysaccharide-induced fulminant hepatic failure.
PubMed:[Effects of ABA on tanshinones accumulation of Salvia miltiorrhiza hairy root].
PubMed:The herbal compound cryptotanshinone restores sensitivity in cancer cells that are resistant to the tumor necrosis factor-related apoptosis-inducing ligand.
PubMed:Identification of cryptotanshinone as an inhibitor of oncogenic protein tyrosine phosphatase SHP2 (PTPN11).
PubMed:Apoptosis Induced by Tanshinone IIA and Cryptotanshinone Is Mediated by Distinct JAK/STAT3/5 and SHP1/2 Signaling in Chronic Myeloid Leukemia K562 Cells.
PubMed:The profiling of bioactive ingredients of differently aged Salvia miltiorrhiza roots.
PubMed:A rapid UFLC-MS/MS method for simultaneous determination of formononetin, cryptotanshinone, tanshinone IIA and emodin in rat plasma and its application to a pharmacokinetic study of Bu Shen Huo Xue formula.
PubMed:Effects of combined elicitors on tanshinone metabolic profiling and SmCPS expression in Salvia miltiorrhiza hairy root cultures.
PubMed:Application of a rapid and efficient quantitative analysis method for traditional Chinese medicines: the case study of quality assessment of Salvia miltiorrhiza Bunge.
PubMed:Cryptotanshinone inhibits human glioma cell proliferation by suppressing STAT3 signaling.
PubMed:Differential androgen deprivation therapies with anti-androgens casodex/bicalutamide or MDV3100/Enzalutamide versus anti-androgen receptor ASC-J9(R) Lead to promotion versus suppression of prostate cancer metastasis.
PubMed:Proapoptotic and TRAIL-sensitizing constituents isolated from Salvia militiorrhiza (Danshen).
PubMed:PF2401-SF, standardized fraction of Salvia miltiorrhiza shows anti-inflammatory activity in macrophages and acute arthritis in vivo.
PubMed:Conical coils counter-current chromatography for preparative isolation and purification of tanshinones from Salvia miltiorrhiza Bunge.
PubMed:Tanshinone IIA and Cryptotanshinone Prevent Mitochondrial Dysfunction in Hypoxia-Induced H9c2 Cells: Association to Mitochondrial ROS, Intracellular Nitric Oxide, and Calcium Levels.
PubMed:Anticancer activity in human multiple myeloma U266 cells: synergy between cryptotanshinone and arsenic trioxide.
PubMed:Qualitative and quantitative analysis of the major constituents in Chinese medicinal preparation Dan-Lou tablet by ultra high performance liquid chromatography/diode-array detector/quadrupole time-of-flight tandem mass spectrometry.
PubMed:Tanshinone I activates the Nrf2-dependent antioxidant response and protects against As(III)-induced lung inflammation in vitro and in vivo.
PubMed:TanshinoneIIA and cryptotanshinone protect against hypoxia-induced mitochondrial apoptosis in H9c2 cells.
PubMed:Cryptotanshinone and dihydrotanshinone I exhibit strong inhibition towards human liver microsome (HLM)-catalyzed propofol glucuronidation.
PubMed:Molecular evidence of cryptotanshinone for treatment and prevention of human cancer.
PubMed:Inhibition of Hypoxia Inducible Factor Alpha and Astrocyte-Elevated Gene-1 Mediates Cryptotanshinone Exerted Antitumor Activity in Hypoxic PC-3 Cells.
PubMed:Enzyme kinetic and molecular docking studies for the inhibitions of miltirone on major human cytochrome P450 isozymes.
PubMed:Tanshinone derivatives: a patent review (January 2006 - September 2012).
PubMed:Coexisted components of Salvia miltiorrhiza enhance intestinal absorption of cryptotanshinone via inhibition of the intestinal P-gp.
PubMed:Comparison of neuroprotective effects of five major lipophilic diterpenoids from Danshen extract against experimentally induced transient cerebral ischemic damage.
PubMed:[Chemical constituents contained in Salvia castanea].
PubMed:Enhancement of solubility and dissolution rate of cryptotanshinone, tanshinone I and tanshinone IIA extracted from Salvia miltiorrhiza.
PubMed:On-line ionic liquid-based dynamic microwave-assisted extraction-high performance liquid chromatography for the determination of lipophilic constituents in root of Salvia miltiorrhiza Bunge.
PubMed:Three-channel column-switching high-performance liquid chromatography with electrochemical detection for determining bioactive redox components in Salvia miltiorrhiza.
PubMed:Cryptotanshinone and tanshinone IIA enhance IL-15-induced natural killer cell differentiation.
PubMed:Metabolism of tanshinone IIA, cryptotanshinone and tanshinone I from Radix Salvia miltiorrhiza in zebrafish.
 
Notes:
from salvia miltiorrhiza. Isol. from Rosmarinus officinalis (rosemary)
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