(1S)-myrtenal
bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-, (1S)-
 
Notes:
None found
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CAS Number: 23727-16-4Picture of molecule3D/inchi
Other(deleted CASRN): 126935-14-6
FDA UNII: 7N44SFN4SS
Nikkaji Web: J16.457G
XlogP3-AA: 2.10 (est)
Molecular Weight: 150.22078000
Formula: C10 H14 O
NMR Predictor: Predict (works with chrome, Edge or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 215.74 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.145000 mmHg @ 25.00 °C. (est)
Flash Point: 174.00 °F. TCC ( 78.90 °C. ) (est)
logP (o/w): 2.756 (est)
Soluble in:
 alcohol
 water, 215.9 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Description:
spicy
 
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 (1S)-myrtenal usage levels up to:
 not for fragrance use.
 
Recommendation for (1S)-myrtenal 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
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 1201528
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 (1S)-6,6-dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde
Chemidplus: 0023727164
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References:
 (1S)-6,6-dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 1201528
Pubchem (sid): 135096444
Flavornet: 23727-16-4
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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
CHEMBL: View
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:
 bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-, (1S)-
(+)-(1S)-6,6-dimethyl bicyclo(3.1.1)hept-2-ene-2-carboxaldehyde
(1S)-6,6-dimethyl bicyclo(3.1.1)hept-2-ene-2-carboxaldehyde
(1S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxaldehyde
(1S)-6,6-dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde
(+)-myrtenal
dextro-myrtenal
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Articles:
PubMed: Four-step synthesis of the antimalarial cardamom peroxide via an oxygen stitching strategy.
PubMed: Anti-inflammatory and chondroprotective activity of (+)-α-pinene: structural and enantiomeric selectivity.
PubMed: Phytochemical and physical-chemical analysis of Polish willow (Salix spp.) honey: identification of the marker compounds.
PubMed: Aroma chemistry of African Oryza glaberrima and Oryza sativa rice and their interspecific hybrids.
PubMed: Production of flavours and fragrances via bioreduction of (4R)-(-)-carvone and (1R)-(-)-myrtenal by non-conventional yeast whole-cells.
PubMed: Chirality transfer based on reversible C-C bond formation/breaking in nickel(II) complexes.
PubMed: Toxicity of Zanthoxylum piperitum and Zanthoxylum armatum oil constituents and related compounds to Stomoxys calcitrans (Diptera: Muscidae).
PubMed: Myrtenal, a natural monoterpene, down-regulates TNF-α expression and suppresses carcinogen-induced hepatocellular carcinoma in rats.
PubMed: Myrtenal attenuates diethylnitrosamine-induced hepatocellular carcinoma in rats by stabilizing intrinsic antioxidants and modulating apoptotic and anti-apoptotic cascades.
PubMed: Aframomum stipulatum (Gagnep) K. Schum and Aframomum giganteum (Oliv. & Hanb) K. Schum as Aroma Tincto Oleo Crops resources: essential oil, fatty acids, sterols, tocopherols, and tocotrienols composition of different fruit parts of Congo varieties.
PubMed: Evaluation of the antinociceptive, anti-inflammatory and gastric antiulcer activities of the essential oil from Piper aleyreanum C.DC in rodents.
PubMed: Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
PubMed: Insertion of T4-lysozyme (T4L) can be a useful tool for studying olfactory-related GPCRs.
PubMed: Myrtenal ameliorates diethylnitrosamine-induced hepatocarcinogenesis through the activation of tumor suppressor protein p53 and regulation of lysosomal and mitochondrial enzymes.
PubMed: Structure and function analyses of the purified GPCR human vomeronasal type 1 receptor 1.
PubMed: Myrtenal inhibits acetylcholinesterase, a known Alzheimer target.
PubMed: Mutual interactions between an invasive bark beetle and its associated fungi.
PubMed: Myrtenal, a controversial molecule for the proper application of the CIP Sequence Rule for multiple bonds.
PubMed: Direct synthesis of NNN-donor enantiopure scorpionate ligands by an efficient diastereoselective nucleophilic addition to imines.
PubMed: Chemical composition and biological activities of Tunisian Cuminum cyminum L. essential oil: a high effectiveness against Vibrio spp. strains.
PubMed: Absolute configuration of (-)-myrtenal by vibrational circular dichroism.
PubMed: Quantitative variation and biosynthesis of hindgut volatiles associated with the red turpentine beetle, Dendroctonus valens LeConte, at different attack phases.
PubMed: [Analysis of essential oil from different organs of Caryopteris tangutica].
PubMed: On the search for NNO-donor enantiopure scorpionate ligands and their coordination to group 4 metals.
PubMed: Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.
PubMed: 25 years of natural product R&D with New South Wales agriculture.
PubMed: Highly diastereoselective nucleophilic addition to myrtenal. Straightforward synthesis of an enantiopure scorpionate ligand.
PubMed: Use of gas chromatography-mass spectrometry combined with resolution methods to characterize the essential oil components of Iranian cumin and caraway.
PubMed: Synthesis of a new (1R)-(-)-myrtenal-derived dioxadithiadodecacycle and its use as an efficient chiral auxiliary.
PubMed: Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.
PubMed: New synthetic routes toward enantiopure nitrogen donor ligands.
PubMed: Synthesis and cytotoxicity of enantiomerically pure [1,2-diamino-1-(4-fluorophenyl)-3-methylbutane]platinum(II) complexes.
PubMed: Chemical composition, seasonal variability, and antifungal activity of Lavandula stoechas L. ssp. stoechas essential oils from stem/leaves and flowers.
PubMed: The nicholas approach to natural product hybrids.
PubMed: Signal separation and determination of the enantiomeric purity of primary amines with (-)-myrtenal--a 13C NMR study.
PubMed: Electrophysiological and behavioral responses of Dendroctonus frontalis (Coleoptera: Curculionidae) to volatiles isolated from conspecifics.
PubMed: Enantiomerically pure [1, 2-diamino-1-(4-fluorophenyl)butane]platinum(II) complexes: synthesis and antitumor activity against MCF-7 and MDA-MB 231 breast cancer and LnCaP/FGC prostate cancer cell lines.
PubMed: Transformation of terpenes using a Picea abies suspension culture.
PubMed: Synthetic routes for a new family of chiral tetradentate ligands containing pyridine rings.
PubMed: New 1,3-oxathianes derived from myrtenal: synthesis and reactivity.
PubMed: Cobalt-mediated approach for the synthesis of terpene-based hybrids.
PubMed: 1H-nuclear magnetic resonance determination of the enantiomeric purity of aliphatic primary amines, beta-aminoalcohols, beta-diamines and alpha-amino-acids with 1R-(-)-myrtenal: scope and limitations.
PubMed: [Chemical constituents in volatile oil from fruits of Alpinia oxyphylla Miq].
PubMed: Ruthenium-catalyzed reaction of alpha,beta-unsaturated imines with carbon monoxide and alkenes leading to beta,gamma-unsaturated gamma-butyrolactams: involvement of direct carbonylation at olefinic C[bond]H Bonds as a key step.
PubMed: Synthesis and antitumor activity of enantiomerically pure [1,2-diamino-1-(4-fluorophenyl)propane]dichloroplatinum(II) complexes.
PubMed: Volatile components of green walnut husks.
PubMed: Decomposition of Terpenes by Ozone during Sampling on Tenax.
PubMed: Methyl salicylate and (-)-(1R,5S)-myrtenal are plant-derived repellents for black bean aphid,Aphis fabae Scop. (Homoptera: Aphididae).
PubMed: Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae).
PubMed: Olfactory sensitivity of two sympatric species of rice leaf folders (Lepidoptera: Pyralidae) to plant volatiles.
PubMed: Hepatic microsomal oxygenation of aldehydes to carboxylic acids.
PubMed: Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits.
PubMed: Secondary attraction and field activity of beetle-produced volatiles inDendroctonus terebrans.
PubMed: Defensive odor emission from larvae of two sawfly species,Pristiphora erichsonii andP. wesmaeli.
PubMed: The pharmacokinetics of the bronchosecretolytic ozothin after intravenous injection.
PubMed: Composition of essential oil of Ledum palustre.
PubMed: Identification and quantitative analysis of the volatile substances emitted by maturing cotton in the field.
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