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515-03-7,MFCD00869558
Catalog No.:AA003U54

515-03-7 | (1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

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1mg
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25mg
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$12.00   $8.00
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50mg
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$14.00   $10.00
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100mg
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$17.00   $12.00
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1g
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$18.00   $13.00
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5g
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$32.00   $23.00
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25g
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$80.00   $56.00
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100g
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500g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003U54
Chemical Name:
(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol
CAS Number:
515-03-7
Molecular Formula:
C20H36O2
Molecular Weight:
308.4986
MDL Number:
MFCD00869558
SMILES:
C=C[C@@](CC[C@H]1[C@](C)(O)CCC2[C@]1(C)CCCC2(C)C)(O)C
Properties
Properties
 
BP:
218-220 °C19 mm Hg(lit.)  
Form:
Solid  
MP:
95-100 °C(lit.)  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
429  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
4  
XLogP3:
4.9  

Literature

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Cancer cell spheroids as a model to evaluate chemotherapy protocols.

Journal: Cancer biology & therapy 20121001

Title: Identification of natural diterpenes that inhibit bacterial wilt disease in tobacco, tomato and Arabidopsis.

Journal: Plant & cell physiology 20120801

Title: Regulators of floral fragrance production and their target genes in petunia are not exclusively active in the epidermal cells of petals.

Journal: Journal of experimental botany 20120501

Title: Synthetic strategies to terpene quinones/hydroquinones.

Journal: Marine drugs 20120201

Title: Sclareol exhibits anti-inflammatory activity in both lipopolysaccharide-stimulated macrophages and the λ-carrageenan-induced paw edema model.

Journal: Journal of natural products 20120127

Title: Four potato (Solanum tuberosum) ABCG transporters and their expression in response to abiotic factors and Phytophthora infestans infection.

Journal: Journal of plant physiology 20111215

Title: Antimicrobial evaluation of diterpenes from Copaifera langsdorffii oleoresin against periodontal anaerobic bacteria.

Journal: Molecules (Basel, Switzerland) 20111118

Title: Synthesis of the scalarane sesterterpenoid 16-deacetoxy-12-epi-scalarafuranacetate.

Journal: The Journal of organic chemistry 20110902

Title: The labdane diterpene sclareol (labd-14-ene-8, 13-diol) induces apoptosis in human tumor cell lines and suppression of tumor growth in vivo via a p53-independent mechanism of action.

Journal: European journal of pharmacology 20110901

Title: Isolation, chemical, and biotransformation routes of labdane-type diterpenes.

Journal: Chemical reviews 20110810

Title: Improving yeast strains using recyclable integration cassettes, for the production of plant terpenoids.

Journal: Microbial cell factories 20110101

Title: Resins and Gums in Historical Iatrosophia Texts from Cyprus - A Botanical and Medico-pharmacological Approach.

Journal: Frontiers in pharmacology 20110101

Title: Triterpenoid biosynthesis and engineering in plants.

Journal: Frontiers in plant science 20110101

Title: Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol.

Journal: Journal of liposome research 20100901

Title: A copal-8-ol diphosphate synthase from the angiosperm Cistus creticus subsp. creticus is a putative key enzyme for the formation of pharmacologically active, oxygen-containing labdane-type diterpenes.

Journal: Plant physiology 20100901

Title: Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa.

Journal: Natural product communications 20100801

Title: Identification and analysis of in planta expressed genes of Magnaporthe oryzae.

Journal: BMC genomics 20100101

Title: Sclareol modulates the Treg intra-tumoral infiltrated cell and inhibits tumor growth in vivo.

Journal: Cellular immunology 20100101

Title: Inhibition of angiogenesis- and inflammation-inducing factors in human colon cancer cells in vitro and in ovo by free and nanoparticle-encapsulated redox dye, DCPIP.

Journal: Journal of nanobiotechnology 20100101

Title: Hemisynthesis of two marine cheilanthane sesterterpenes from (-)-sclareol: first enantioselective synthesis of petrosaspongiolide R.

Journal: Natural product research 20090101

Title: Fragrance material review on sclareol.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20081101

Title: Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro.

Journal: Planta medica 20071001

Title: Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice.

Journal: Apoptosis : an international journal on programmed cell death 20070401

Title: Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products.

Journal: Pakistan journal of pharmaceutical sciences 20070401

Title: Calorimetric study on the induction of interdigitated phase in hydrated DPPC bilayers by bioactive labdanes and correlation to their liposome stability: The role of chemical structure.

Journal: Chemistry and physics of lipids 20070101

Title: Liposomes modify the subcellular distribution of sclareol uptake by HCT-116 cancer cell lines.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20070101

Title: Hemisynthesis of new labdane derivatives from (-)-sclareol.

Journal: Natural product research 20060801

Title: Synthesis of ent-thallusin.

Journal: Organic letters 20060511

Title: Labd-14-ene-8,13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20060401

Title: Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts.

Journal: Pharmacological research 20060101

Title: Structure elucidation and antibacterial activity of new fungal metabolites of sclareol.

Journal: Chemistry & biodiversity 20060101

Title: NpPDR1, a pleiotropic drug resistance-type ATP-binding cassette transporter from Nicotiana plumbaginifolia, plays a major role in plant pathogen defense.

Journal: Plant physiology 20050901

Title: Microbial hydroxylation of sclareol by Rhizopus stolonifer.

Journal: Molecules (Basel, Switzerland) 20050831

Title: First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol.

Journal: Organic letters 20050414

Title: A comparative study of the effects of cholesterol and sclareol, a bioactive labdane type diterpene, on phospholipid bilayers.

Journal: Chemistry and physics of lipids 20050201

Title: Effect of 13-epi-sclareol on the bacterial respiratory chain.

Journal: Planta medica 20041101

Title: Pathogen-responsive expression of a putative ATP-binding cassette transporter gene conferring resistance to the diterpenoid sclareol is regulated by multiple defense signaling pathways in Arabidopsis.

Journal: Plant physiology 20031101

Title: Identification of regulatory sequence elements within the transcription promoter region of NpABC1, a gene encoding a plant ABC transporter induced by diterpenes.

Journal: The Plant journal : for cell and molecular biology 20030701

Title: A study on the synthesis of antiangiogenic (+)-coronarin A and congeners from (+)-sclareolide.

Journal: Bioorganic & medicinal chemistry letters 20030616

Title: The plant PDR family of ABC transporters.

Journal: Planta 20021101

Title: Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.

Journal: Molecular pharmacology 20021001

Title: The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol.

Journal: The Plant journal : for cell and molecular biology 20020601

Title: Antibacterial diterpenoids from Astragalus brachystachys.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101

Title: Antimycobacterial plant terpenoids.

Journal: Planta medica 20011101

Title: A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion.

Journal: The Plant cell 20010501

Title: Structure elucidation and conformational properties of a novel bioactive clerodane diterpene using a combination of high field NMR spectroscopy, computational analysis and X-ray diffraction.

Journal: Bioorganic & medicinal chemistry letters 20010326

Title: Chromatographic (GC-MS, HPLC) and virological evaluations of Salvia sclarea infected by BBWV-I.

Journal: Farmaco (Societa chimica italiana : 1989) 20010301

Title: Diterpenes from the berries of Juniperus excelsa.

Journal: Phytochemistry 19990401

Title: Robert Tisserand, et al. Sclareol.Constituent profiles

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Tags:515-03-7 Molecular Formula|515-03-7 MDL|515-03-7 SMILES|515-03-7 (1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol