myrtenal
2-formyl-6,6-dimethylbicyclo[3.1.1]hept-2-ene (myrtenal)
Identification
| Name | myrtenal |
| IUPAC | 7,7-dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde |
| CAS Number | 564-94-3 |
| EINECS | 209-274-8 |
| FDA UNII | 8J97443QRZ |
| Molecular Formula | C10 H14 O |
| Molecular Weight | 150.22078000 |
| MDL Number | MFCD00074768 |
| Nikkaji Number | J121.133A |
| Beilstein | 2961587 |
| CoE Number | 10379 |
Regulatory
| JECFA Food Flavoring | 980 2-formyl-6,6-dimethylbicyclo[3.1.1]hept-2-ene (myrtenal) |
| DG SANTE Food Flavourings | 05.106 myrtenal |
| FEMA Number | 3395 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 564-94-3 ; 2-FORMYL-6,6-DIMETHYLBICYCLO(3.1.1)HEPT-2-ENE |
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.98400 to 0.99000 @ 25.00 °C. |
| Pounds per Gallon - (est). | 8.188 to 8.238 |
| Refractive Index | 1.49600 to 1.50700 @ 20.00 °C. |
| Boiling Point | 220.00 to 221.00 °C. @ 760.00 mm Hg, 99.00 to 100.00 °C. @ 15.00 mm Hg |
| Vapor Pressure | 0.145000 mmHg @ 25.00 °C. (est) |
| Flash Point | 174.00 °F. TCC ( 78.89 °C. ) |
| logP (o/w) | 2.980 |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Strength | medium |
| Substantivity | 48 hour(s) at 100.00 % |
| Odor Description |
at 100.00 %. Cooling, green, minty with spicy woody notes
|
| Odor sample from | Sigma-Aldrich |
| Taste Description | at 30.00 ppm. |
Safety Information
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 2300 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 > 5000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for myrtenal usage levels up to | 2.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 2.20 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 7.00 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 1700 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
| Dairy products, excluding products of category 02.0 (01.0) | 1.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 8.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 2.00000 |
| Processed fruit (04.1) | 1.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | 5.00000 |
| Confectionery (05.0) | 20.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 1.00000 |
| Bakery wares (07.0) | 5.00000 |
| Meat and meat products, including poultry and game (08.0) | 1.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 1.00000 |
| Eggs and egg products (10.0) | 1.00000 |
| Sweeteners, including honey (11.0) | 1.00000 |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | - |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 1.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 1.00000 |
| Ready-to-eat savouries (15.0) | 1.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 1.00000 |
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Potential Uses
Natural Occurrence
Synonyms
benihinal
bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-
6,6-
dimethyl bicyclo(3.1.1)hept-2-ene-2-carboxaldehyde
6,6-
dimethyl-2-norpinene-2-carboxaldehyde
6,6-
dimethylbicyclo(3.1.1)hept-2-ene-2-carboxaldehyde
6,6-
dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
6,6-
dimethylbicyclo[3.1.1]hept-2-ene-2-carboxaldehyde
7,7-
dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde
2-
formyl-6,6-dimethyl bicyclo(3.1.1)hept-2-ene
2-
formyl-6,6-dimethyl-2-norpinene
2-
formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene
2-
formyl-6,6-dimethylbicyclo[3.1.1]hept-2-ene (myrtenal)
(±)-
myrtenal
pin-2-ene-1-carbaldehyde
2-nor
pinene-2-carboxaldehyde, 6,6-dimethyl-
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.