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515-03-7 | Sclareol
CAS No: 515-03-7 Catalog No: AG003U7W MDL No:MFCD00869558
Product Description
Catalog Number:
AG003U7W
Chemical Name:
Sclareol
CAS Number:
515-03-7
Molecular Formula:
C20H36O2
Molecular Weight:
308.4986
MDL Number:
MFCD00869558
IUPAC Name:
(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
InChI:
InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
InChI Key:
XVULBTBTFGYVRC-HHUCQEJWSA-N
SMILES:
C=C[C@@](CC[C@H]1[C@](C)(O)CCC2[C@]1(C)CCCC2(C)C)(O)C
EC Number:
208-194-0
UNII:
B607NP0Q8Y
Properties
Complexity:
429
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
5
Defined Bond Stereocenter Count:
0
Exact Mass:
308.272g/mol
Formal Charge:
0
Heavy Atom Count:
22
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
308.506g/mol
Monoisotopic Mass:
308.272g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
40.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.9
Literature
| Title | Journal |
|---|---|
| Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. | Bioorganic & medicinal chemistry 20121115 |
| Cancer cell spheroids as a model to evaluate chemotherapy protocols. | Cancer biology & therapy 20121001 |
| Identification of natural diterpenes that inhibit bacterial wilt disease in tobacco, tomato and Arabidopsis. | Plant & cell physiology 20120801 |
| Regulators of floral fragrance production and their target genes in petunia are not exclusively active in the epidermal cells of petals. | Journal of experimental botany 20120501 |
| Synthetic strategies to terpene quinones/hydroquinones. | Marine drugs 20120201 |
| Sclareol exhibits anti-inflammatory activity in both lipopolysaccharide-stimulated macrophages and the λ-carrageenan-induced paw edema model. | Journal of natural products 20120127 |
| Four potato (Solanum tuberosum) ABCG transporters and their expression in response to abiotic factors and Phytophthora infestans infection. | Journal of plant physiology 20111215 |
| Antimicrobial evaluation of diterpenes from Copaifera langsdorffii oleoresin against periodontal anaerobic bacteria. | Molecules (Basel, Switzerland) 20111118 |
| Synthesis of the scalarane sesterterpenoid 16-deacetoxy-12-epi-scalarafuranacetate. | The Journal of organic chemistry 20110902 |
| 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. | European journal of pharmacology 20110901 |
| Isolation, chemical, and biotransformation routes of labdane-type diterpenes. | Chemical reviews 20110810 |
| Improving yeast strains using recyclable integration cassettes, for the production of plant terpenoids. | Microbial cell factories 20110101 |
| Resins and Gums in Historical Iatrosophia Texts from Cyprus - A Botanical and Medico-pharmacological Approach. | Frontiers in pharmacology 20110101 |
| Triterpenoid biosynthesis and engineering in plants. | Frontiers in plant science 20110101 |
| Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol. | Journal of liposome research 20100901 |
| 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. | Plant physiology 20100901 |
| Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa. | Natural product communications 20100801 |
| Identification and analysis of in planta expressed genes of Magnaporthe oryzae. | BMC genomics 20100101 |
| Sclareol modulates the Treg intra-tumoral infiltrated cell and inhibits tumor growth in vivo. | Cellular immunology 20100101 |
| 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 of nanobiotechnology 20100101 |
| Hemisynthesis of two marine cheilanthane sesterterpenes from (-)-sclareol: first enantioselective synthesis of petrosaspongiolide R. | Natural product research 20090101 |
| Fragrance material review on sclareol. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20081101 |
| Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro. | Planta medica 20071001 |
| Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice. | Apoptosis : an international journal on programmed cell death 20070401 |
| Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products. | Pakistan journal of pharmaceutical sciences 20070401 |
| 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. | Chemistry and physics of lipids 20070101 |
| Liposomes modify the subcellular distribution of sclareol uptake by HCT-116 cancer cell lines. | Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20070101 |
| Hemisynthesis of new labdane derivatives from (-)-sclareol. | Natural product research 20060801 |
| Synthesis of ent-thallusin. | Organic letters 20060511 |
| 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. | Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20060401 |
| Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts. | Pharmacological research 20060101 |
| Structure elucidation and antibacterial activity of new fungal metabolites of sclareol. | Chemistry & biodiversity 20060101 |
| NpPDR1, a pleiotropic drug resistance-type ATP-binding cassette transporter from Nicotiana plumbaginifolia, plays a major role in plant pathogen defense. | Plant physiology 20050901 |
| Microbial hydroxylation of sclareol by Rhizopus stolonifer. | Molecules (Basel, Switzerland) 20050831 |
| First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol. | Organic letters 20050414 |
| A comparative study of the effects of cholesterol and sclareol, a bioactive labdane type diterpene, on phospholipid bilayers. | Chemistry and physics of lipids 20050201 |
| Effect of 13-epi-sclareol on the bacterial respiratory chain. | Planta medica 20041101 |
| 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. | Plant physiology 20031101 |
| Identification of regulatory sequence elements within the transcription promoter region of NpABC1, a gene encoding a plant ABC transporter induced by diterpenes. | The Plant journal : for cell and molecular biology 20030701 |
| A study on the synthesis of antiangiogenic (+)-coronarin A and congeners from (+)-sclareolide. | Bioorganic & medicinal chemistry letters 20030616 |
| The plant PDR family of ABC transporters. | Planta 20021101 |
| Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit. | Molecular pharmacology 20021001 |
| The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol. | The Plant journal : for cell and molecular biology 20020601 |
| Antibacterial diterpenoids from Astragalus brachystachys. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101 |
| Antimycobacterial plant terpenoids. | Planta medica 20011101 |
| A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion. | The Plant cell 20010501 |
| 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. | Bioorganic & medicinal chemistry letters 20010326 |
| Chromatographic (GC-MS, HPLC) and virological evaluations of Salvia sclarea infected by BBWV-I. | Farmaco (Societa chimica italiana : 1989) 20010301 |
| Diterpenes from the berries of Juniperus excelsa. | Phytochemistry 19990401 |
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