totarol
2-phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS,8aS)-
 
Notes:
isolated from the bark of podocarpus nagi.
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      Product(s):
      TOTAROL
      TOTAROL K7 LIQUID
       
Synonyms   Articles   Notes   Search
(4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol (Click)
CAS Number: 511-15-9Picture of molecule
FDA UNII: 67NH2854WW
Nikkaji Web: J14.012K
MDL: MFCD02094185
XlogP3-AA: 6.70 (est)
Molecular Weight: 286.45830000
Formula: C20 H30 O
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: white solid (est)
Assay: 97.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 128.00 to  132.00 °C. @ 760.00 mm Hg
Boiling Point: 369.00 to  371.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.000005 mm/Hg @ 25.00 °C. (est)
Flash Point: 332.00 °F. TCC ( 166.67 °C. )
logP (o/w): 6.405 (est)
Soluble in:
 alcohol
 water, 0.03402 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
deodorants
oral care agents
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Suppliers:
BOC Sciences
For experimental / research use only.
Totarol >98%
Odor: characteristic
Use: Totarol is a naturally produced diterpenoid isolated from the barks of Podocarpus totara. Recent studies show that (+)-totarol has unique antimicrobial and therapeutic properties. anti-bacteria
Charkit Chemical
TOTAROL K7 LIQUID
Charkit Chemical
TOTAROL
Santa Cruz Biotechnology
For experimental / research use only.
(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol
Sigma-Aldrich: Aldrich
For experimental / research use only.
4bS-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropyl-phenanthren-2-ol 98%
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Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
 
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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for totarol usage levels up to:
 not for fragrance use.
 
Recommendation for totarol flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 92783
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
Chemidplus: 0000511159
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References:
 (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 92783
Pubchem (sid): 135049775
Pherobase: View
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (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
HMDB (The Human Metabolome Database): Search
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cedar western red cedar
Search Trop  Picture
 cedarleaf oil canada @ trace-0.10%
Data  GC  Search Trop  Picture
 ferula communis
Search Trop  Picture
 juniperus procera
Search Trop  Picture
 plumbago zeylanica
Search Trop  Picture
 podocarpus nagi
Search Trop  Picture
 podocorpus totara g. benn.
Search Trop  Picture
 rosemary oil CO2 extract @ trace%
Data  GC  Search Trop  Picture
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Synonyms:
4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methyl ethyl)-2-phenanthrenol
4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenol
2-phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS-trans)-
2-phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS,8aS)-
14-isopropyl podocarpa-8,11,13-trien-13-ol
(4bS,8aS)-4b,8,8-trimethyl-1-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-ol
(4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
4bS-trans-8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropyl-phenanthren-2-ol
(4bS)-trans-8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol
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Articles:
PubMed: Totarol prevents neuronal injury in vitro and ameliorates brain ischemic stroke: Potential roles of Akt activation and HO-1 induction.
PubMed: The synergy of berberine chloride and totarol against Staphylococcus aureus grown in planktonic and biofilm cultures.
PubMed: Inhibitory effect of totarol on exotoxin proteins hemolysin and enterotoxins secreted by Staphylococcus aureus.
PubMed: Phenolic diterpenoid derivatives as anti-influenza a virus agents.
PubMed: A comprehensive proteomic analysis of totarol induced alterations in Bacillus subtilis by multipronged quantitative proteomics.
PubMed: (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa-hydro-phenan-thren-2-yl benzoate.
PubMed: Preparative mass-spectrometry profiling of bioactive metabolites in Saudi-Arabian propolis fractionated by high-speed countercurrent chromatography and off-line atmospheric pressure chemical ionization mass-spectrometry injection.
PubMed: (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa-hydro-phenan-thren-2-yl acetate.
PubMed: More insight into the chemical composition of Greek propolis; differences and similarities with Turkish propolis.
PubMed: Inhibitors of bacterial tubulin target bacterial membranes in vivo.
PubMed: Extraction of essential oil from Cupressus sempervirens: comparison of global yields, chemical composition and antioxidant activity obtained by hydrodistillation and supercritical extraction.
PubMed: The Synthesis and Antimicrobial Activity of Heterocyclic Derivatives of Totarol.
PubMed: Composition and antipathogenic activities of the twig essential oil of Chamaecyparis formosensis from Taiwan.
PubMed: Synthesis, biological evaluation and mechanistic studies of totarol amino alcohol derivatives as potential antimalarial agents.
PubMed: Biota: sediment partitioning of aluminium smelter related PAHs and pulp mill related diterpenes by intertidal clams at Kitimat, British Columbia.
PubMed: Composition, antioxidant and antimicrobial activities of the seed essential oil of Calocedrus formosana from Taiwan.
PubMed: Molecular basis of the anti-inflammatory property exhibited by cyclo-pentano phenanthrenol isolated from Lippia nodiflora.
PubMed: Synthesis of antimicrobial natural products targeting FtsZ: (+)-totarol and related totarane diterpenes.
PubMed: Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae).
PubMed: Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.
PubMed: Antibacterial novel phenolic diterpenes from Podocarpus macrophyllus D. Don.
PubMed: Assessment of some diterpenoids in commercial distilled gin.
PubMed: Antifibrotic activity of diterpenes from Biota orientalis leaves on hepatic stellate cells.
PubMed: Synthesis of totarane diterpenes: totarol, maytenoquinone, 6-deoxymaytenoquinone and 8,11,13-totaratriene-12,13-diol.
PubMed: The antifungal compound totarol of Thujopsis dolabrata var. hondai seeds selects for fungi on seedling root surfaces.
PubMed: Occurrence and estrogenicity of phenolics in paper-recycling process water: pollutants originating from thermal paper in waste paper.
PubMed: The phenolic diterpene totarol inhibits multidrug efflux pump activity in Staphylococcus aureus.
PubMed: Totarol inhibits bacterial cytokinesis by perturbing the assembly dynamics of FtsZ.
PubMed: Gastroprotective and cytotoxic effect of semisynthetic ferruginol derivatives.
PubMed: Cytotoxic diterpenoids from Podocarpus madagascariensis from the Madagascar rainforest.
PubMed: Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide.
PubMed: Novel domino reactions for diterpene synthesis.
PubMed: Antineoplastic agents. 529. Isolation and structure of nootkastatins 1 and 2 from the Alaskan yellow cedar Chamaecyparis nootkatensis.
PubMed: Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity.
PubMed: Development of a method to quantify in vitro the synergistic activity of "natural" antimicrobials.
PubMed: The propolis of stingless bees: terpenes from the tibia of three Frieseomelitta species.
PubMed: A MAS-NMR study of the location of (+)-totarol, a diterpenoid bioactive molecule, in phospholipid model membranes.
PubMed: Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii.
PubMed: A cyclic peroxide of clerodenoic acid from the Taiwanese liverwort Schistochila acuminata.
PubMed: (+)-Totarol from Chamaecyparis nootkatensis and activity against Mycobacterium tuberculosis.
PubMed: Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae).
PubMed: Effects of (+)-totarol, a diterpenoid antibacterial agent, on phospholipid model membranes.
PubMed: A fluorescence study of the interaction and location of (+)-totarol, a diterpenoid bioactive molecule, in model membranes.
PubMed: Totarol, totaradiol and ferruginol: three diterpenes from Thuja plicata (Cupressaceae).
PubMed: The synthesis and antibacterial activity of totarol derivatives. Part 3: Modification of ring-B.
PubMed: The synthesis and antibacterial activity of totarol derivatives. Part 2: Modifications at C-12 and O-13.
PubMed: The synthesis and antibacterial activity of totarol derivatives. Part 1: modifications of ring-C and pro-drugs.
PubMed: Potentiation of methicillin activity against methicillin-resistant Staphylococcus aureus by diterpenes.
PubMed: Antioxidative action of diterpenoids from Podocarpus nagi.
PubMed: Inhibition of lipid peroxidation by diterpenoid from Podocarpus nagi.
PubMed: Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus.
PubMed: Mode of antibacterial action of totarol, a diterpene from Podocarpus nagi.
PubMed: Isolation and characterization of platelet-activating factor receptor binding antagonists from Biota orientalis.
PubMed: Antibacterial activity of totarol and its potentiation.
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