5-epi-aristolochene
8.4betaH-eremophila-9,11-diene
 
Notes:
None found
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CAS not foundNF0528Picture of molecule3D/inchi
Nikkaji Web: J275.993D
XlogP3-AA: 5.20 (est)
Molecular Weight: 204.35628000
Formula: C15 H24
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 0.05011 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
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 5-epi-aristolochene usage levels up to:
 not for fragrance use.
 
Recommendation for 5-epi-aristolochene flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Laboratory Chemical Safety Summary : 5460659
 (4R,4aR,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene
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References:
 (4R,4aR,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5460659
Pubchem (cas): NF0528
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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
KEGG (GenomeNet): C19708
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: 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
 found in nature
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Synonyms:
(4R,4aR,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene
8.4betaH-eremophila-9,11-diene
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Articles:
PubMed: Expansion of sesquiterpene biosynthetic gene clusters in pepper confers nonhost resistance to the Irish potato famine pathogen.
PubMed: Biosynthetic potential of sesquiterpene synthases: product profiles of Egyptian Henbane premnaspirodiene synthase and related mutants.
PubMed: The Full-Size ABCG Transporters Nb-ABCG1 and Nb-ABCG2 Function in Pre- and Postinvasion Defense against Phytophthora infestans in Nicotiana benthamiana.
PubMed: Molecular Dynamics Simulations Elucidate Conformational Dynamics Responsible for the Cyclization Reaction in TEAS.
PubMed: Formation of a Novel Macrocyclic Alkaloid from the Unnatural Farnesyl Diphosphate Analogue Anilinogeranyl Diphosphate by 5-Epi-Aristolochene Synthase.
PubMed: Developmentally regulated sesquiterpene production confers resistance to Colletotrichum gloeosporioides in ripe pepper fruits.
PubMed: (+)-Valencene production in Nicotiana benthamiana is increased by down-regulation of competing pathways.
PubMed: Phytoalexin biosynthesis genes are regulated and involved in plant response to Ralstonia solanacearum infection.
PubMed: Induced-fit mechanism in class I terpene cyclases.
PubMed: S-carvone suppresses cellulase-induced capsidiol production in Nicotiana tabacum by interfering with protein isoprenylation.
PubMed: Inhibitory effect of esterified lactoferin and lactoferrin against tobacco mosaic virus (TMV) in tobacco seedlings.
PubMed: Inhibitory effect of sulfated lentinan and lentinan against tobacco mosaic virus (TMV) in tobacco seedlings.
PubMed: De novo synthesis of high-value plant sesquiterpenoids in yeast.
PubMed: Computational design and selections for an engineered, thermostable terpene synthase.
PubMed: Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate.
PubMed: Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphates.
PubMed: Molecular and structural basis of metabolic diversity mediated by prenyldiphosphate converting enzymes.
PubMed: Abscisic acid negatively regulates elicitor-induced synthesis of capsidiol in wild tobacco.
PubMed: A structural model of the membrane-bound aromatic prenyltransferase UbiA from E. coli.
PubMed: Unearthing the roots of the terpenome.
PubMed: Interception of the enzymatic conversion of farnesyl diphosphate to 5-epi-aristolochene by using a fluoro substrate analogue: 1-fluorogermacrene A from (2E,6Z)-6-fluorofarnesyl diphosphate.
PubMed: Functional characterization of premnaspirodiene oxygenase, a cytochrome P450 catalyzing regio- and stereo-specific hydroxylations of diverse sesquiterpene substrates.
PubMed: X-ray crystal structure of aristolochene synthase from Aspergillus terreus and evolution of templates for the cyclization of farnesyl diphosphate.
PubMed: Biosynthetic potential of sesquiterpene synthases: alternative products of tobacco 5-epi-aristolochene synthase.
PubMed: Surrogate splicing for functional analysis of sesquiterpene synthase genes.
PubMed: Molecular recognition of the substrate diphosphate group governs product diversity in trichodiene synthase mutants.
PubMed: A single-vial analytical and quantitative gas chromatography-mass spectrometry assay for terpene synthases.
PubMed: Probing sesquiterpene hydroxylase activities in a coupled assay with terpene synthases.
PubMed: Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene.
PubMed: Structure, mechanism and function of prenyltransferases.
PubMed: Isolation and characterization of two germacrene A synthase cDNA clones from chicory.
PubMed: Gene expression of 5-epi-aristolochene synthase and formation of capsidiol in roots of Nicotiana attenuata and N. sylvestris.
PubMed: The in vivo synthesis of plant sesquiterpenes by Escherichia coli.
PubMed: Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum).
PubMed: Amorpha-4,11-diene synthase of Artemisia annua: cDNA isolation and bacterial expression of a terpene synthase involved in artemisinin biosynthesis.
PubMed: Crystal structure of human squalene synthase. A key enzyme in cholesterol biosynthesis.
PubMed: Cloning and bacterial expression of sesquiterpene cyclase, a key branch point enzyme for the synthesis of sesquiterpenoid phytoalexin capsidiol in UV-challenged leaves of Capsicum annuum.
PubMed: Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase.
PubMed: Pre-steady-state study of recombinant sesquiterpene cyclases.
PubMed: Characterization of Novel Sesquiterpenoid Biosynthesis in Tobacco Expressing a Fungal Sesquiterpene Synthase.
PubMed: cDNA cloning, characterization, and functional expression of 4S-(-)-limonene synthase from Perilla frutescens.
PubMed: Identifying functional domains within terpene cyclases using a domain-swapping strategy.
PubMed: Developmental and stress regulation of gene expression for plastid and cytosolic isoprenoid pathways in pepper fruits.
PubMed: Cloning and bacterial expression of a sesquiterpene cyclase from Hyoscyamus muticus and its molecular comparison to related terpene cyclases.
PubMed: Expression of a plant sesquiterpene cyclase gene in Escherichia coli.
PubMed: Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants.
PubMed: Gene family for an elicitor-induced sesquiterpene cyclase in tobacco.
PubMed: Purification and characterization of an inducible sesquiterpene cyclase from elicitor-treated tobacco cell suspension cultures.
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