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miltirone
3,4-phenanthrenedione, 5,6,7,8-tetrahydro-8,8-dimethyl-2-(1-methylethyl)-

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Name:8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione
CAS Number: 27210-57-7Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J17.268E
XlogP3-AA:4.90 (est)
Molecular Weight:282.38274000
Formula:C19 H22 O2
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:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 421.00 to 422.00 °C. @ 760.00 mm Hg
Flash Point: 354.00 °F. TCC ( 178.89 °C. )
logP (o/w): 4.916 (est)
Soluble in:
 water, 0.05297 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.
miltirone 98%
BOC Sciences
For experimental / research use only.
Miltirone >98%
Odor: characteristic
Use: Source from root of Salvia miltiorrhiza Bge. Miltirone may be a promising candidate for cancer chemotherapy. And it is the likely active constituent of S. miltiorrhiza responsible for the reducing effect of its extracts on alcohol intake in different exp Resistance to atherosclerosis and cardiac protection
Carbosynth
For experimental / research use only.
Miltirone
Coompo
For experimental / research use only.
Miltirone from Plants ≥98%
Odor: characteristic
Use: Pure miltirone reduced alcohol intake in alcohol-experienced rats and delayed acquisition of alcohol-drinking behavior in alcohol-naive rats. Similar to S. miltiorrhiza extracts, miltirone markedly reduced blood alcohol levels when alcohol was administered i.g. but not i.p., suggesting that miltirone hampered alcohol absorption from the gastrointestinal system. Finally, miltirone failed to affect the severity of alcohol withdrawal syndrome in alcohol-dependent rats. suggest that miltirone is the likely active constituent of S. miltiorrhiza responsible for the reducing effect of its extracts on alcohol intake in different experimental models of excessive alcohol consumption. Miltirone has been characterized as a low-affinity ligand for central benzodiazepine receptors. This compound bound with low affinity (micromolar range) to central benzodiazepine recognition sites but did not interact with peripheral benzodiazepine receptors. It failed to potentiate Cl(-) currents induced by gamma-aminobutyric acid (GABA) both in Xenopus oocytes expressing recombinant human GABA(A) receptors and in cultured rat hippocampal pyramidal cells, but it inhibited the ability of diazepam to potentiate the effect of GABA in these systems. Miltirone (1-10 microM) also partially inhibited the increase in the abundance of the mRNA for the alpha subunit of the GABA(A) receptor induced by ethanol withdrawal in cultured hippocampal neurons. These results suggest that miltirone might ameliorate the symptoms associated with discontinuation of long-term administration of ethanol or of other positive modulators of the GABA(A) receptor. Unlike diazepam, miltirone behaved as a partial agonist in the central benzodiazepine receptor binding and behavioural tests. Moreover, it produced no acute muscle relaxant effect and did not induce drug dependence and withdrawal reactions after chronic administration in mice.
Dalton Pharma Services
For experimental / research use only.
Rosmariquinone >95%
Santa Cruz Biotechnology
For experimental / research use only.
Miltirone
 
Safety Information:
European information :
Most important hazard(s):
Xi - Irritant
R 10 - Flammable.
 
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 miltirone usage levels up to:
 not for fragrance use.
 
Recommendation for miltirone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :160142
National Institute of Allergy and Infectious Diseases:Data
8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione
Chemidplus:0027210577
 
References:
 8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):160142
Pubchem (sid):135115917
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C13715
HMDB (The Human Metabolome Database):HMDB35080
FooDB:FDB013705
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 rosemary leaf
Search Trop Picture
 rosemary plant
Search Trop Picture
 salvis miltiorrhiza bunge
Search Trop Picture
 
Synonyms:
8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione
3,4-phenanthrenedione, 5,6,7,8-tetrahydro-8,8-dimethyl-2-(1-methylethyl)-
2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-3,4-phenanthrenedione
2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-phenanthrene-3,4-dione
2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione
 rosmariquinone
5,6,7,8-tetrahydro-8,8-dimethyl-2-(1-methyl ethyl)-3,4-phenanthrene dione
 

Articles:

PubMed:Effects of tanshinones from Salvia miltiorrhiza on CYP2C19 activity in human liver microsomes: Enzyme kinetic and molecular docking studies.
PubMed:Metabolic profile of miltirone in rats by high performance liquid chromatography/quadrupole time-of-flight mass spectrometry.
PubMed:A simple and sensitive LC-MS/MS method for determination of miltirone in rat plasma and its application to pharmacokinetic studies.
PubMed:Reversal of P-glycoprotein (P-gp) mediated multidrug resistance in colon cancer cells by cryptotanshinone and dihydrotanshinone of Salvia miltiorrhiza.
PubMed:Enzyme kinetic and molecular docking studies for the inhibitions of miltirone on major human cytochrome P450 isozymes.
PubMed:Tanshinones as selective and slow-binding inhibitors for SARS-CoV cysteine proteases.
PubMed:[Chemical constituents from Salvia przewalskii Maxim].
PubMed:Extraction and preparative purification of tanshinones from Salvia miltiorrhiza Bunge by high-speed counter-current chromatography.
PubMed:Antiplasmodial and antitrypanosomal activity of tanshinone-type diterpenoids from Salvia miltiorrhiza.
PubMed:[Advances in studies on antitumor activities of compounds in Salvia miltiorrhiza].
PubMed:Characterization of tanshinones with quinone reductase induction activity from Radix Salvia miltiorrhiza by liquid chromatography/tandem mass spectrometry.
PubMed:Phytochemistry and pharmacogenomics of natural products derived from traditional Chinese medicine and Chinese materia medica with activity against tumor cells.
PubMed:Optimizing ultraperformance liquid chromatographic analysis of 10 diterpenoid compounds in Salvia miltiorrhiza using central composite design.
PubMed:Determination of fifteen bioactive components in Radix et Rhizoma Salviae Miltiorrhizae by high-performance liquid chromatography with ultraviolet and mass spectrometric detection.
PubMed:Identification of miltirone as active ingredient of Salvia miltiorrhiza responsible for the reducing effect of root extracts on alcohol intake in rats.
PubMed:Synthesis of miltirone analogues as inhibitors of Cdc25 phosphatases.
PubMed:Inhibition by miltirone of up-regulation of GABAA receptor alpha4 subunit mRNA by ethanol withdrawal in hippocampal neurons.
PubMed:Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method.
PubMed:Apianane terpenoids from Salvia officinalis.
PubMed:Miltirone, a central benzodiazepine receptor partial agonist from a Chinese medicinal herb Salvia miltiorrhiza.
PubMed:Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen).
PubMed:[Chemical studies of Salvia miltiorrhiza f. alba].
 
Notes:
from salvis miltiorrhiza bunge; central benzodiazepine receptor ligand. Constit. of roots of Salvia miltiorrhiza (Chinese sage). Also present in leaves of rosemary (Rosmarinus officinalis). Antioxidant
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