Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Appearance: | colorless clear liquid (est) |
Assay: | 98.00 to 100.00 %
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Food Chemicals Codex Listed: | No |
Specific Gravity: | 0.98400 to 0.99000 @ 25.00 °C.
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Pounds per Gallon - (est).: | 8.188 to 8.238
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Refractive Index: | 1.49600 to 1.50700 @ 20.00 °C.
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Boiling Point: | 220.00 to 221.00 °C. @ 760.00 mm Hg
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Boiling Point: | 99.00 to 100.00 °C. @ 15.00 mm Hg
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Vapor Pressure: | 0.145000 mmHg @ 25.00 °C. (est) |
Flash Point: | 174.00 °F. TCC ( 78.89 °C. )
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logP (o/w): | 2.980 |
Soluble in: |
| alcohol | | dipropylene glycol | | water, 215.9 mg/L @ 25 °C (est) |
Insoluble in: |
| water |
Organoleptic Properties:
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Odor Type: spicy |
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Odor Strength: | medium |
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Substantivity: | 48 hour(s) at 100.00 % |
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| sweet spicy cinnamon tonka terpenic camphoreous jammy |
Odor Description: at 100.00 %. | sweet cinnamon tonka spicy terpene camphor jam Luebke, William tgsc, (1996) |
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| cooling green minty spicy woody |
Odor Description:
| Cooling, green, minty with spicy woody notes Mosciano, Gerard P&F 15, No. 1, 19, (1990) |
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Flavor Type: minty |
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| minty green cooling powdery spicy |
Taste Description: at 30.00 ppm. | Minty, green and cooling with powdery spicy notes Mosciano, Gerard P&F 15, No. 1, 19, (1990) |
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Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
BOC Sciences |
For experimental / research use only. |
Bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde,6,6-dimethyl-
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Ernesto Ventós |
MYRTENAL
Odor: REFRESHING, HERBACEOUS, SPICY |
Frutarom |
MYRTENAL
KOSHER Flavor: Sweet, Spicy, Terpenic, Green, Cooling |
IFF |
MYRTENAL
KOSHER Flavor: Sweet, Spicy, Terpenic, Green, Cooling |
Lluch Essence |
MYRTENAL
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Moellhausen |
MYRTENAL
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Nippon Terpene Chemicals |
Myrtenal 93% up
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Penta International |
MYRTENAL
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Synerzine |
Myrtenal
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Safety Information:
European information : |
Most important hazard(s): | None - None found. |
S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes.
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Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
None found. |
GHS Label elements, including precautionary statements |
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Pictogram | |
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Hazard statement(s) |
None found. |
Precautionary statement(s) |
None found. |
Oral/Parenteral Toxicity: |
oral-rat LD50 2300 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 329, 1988.
intravenous-mouse LD50 170 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 329, 1988.
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Dermal Toxicity: |
skin-rabbit LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 329, 1988.
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Inhalation Toxicity: |
Not determined
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Safety in Use Information:
Category: | flavor and fragrance agents |
RIFM Fragrance Material Safety Assessment: Search |
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice |
Recommendation for myrtenal usage levels up to: | | 2.0000 % in the fragrance concentrate.
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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 |
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). |
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library |
publication number: 7 |
Click here to view publication 7 |
| average usual ppm | average maximum ppm |
baked goods: | - | - |
beverages(nonalcoholic): | - | 0.50000 |
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: | - | 2.00000 |
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: | - | - |
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Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). |
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. |
| average usage mg/kg | maximum usage mg/kg |
Dairy products, excluding products of category 02.0 (01.0): | 1.00000 | 5.00000 |
Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 8.00000 | 50.00000 |
Edible ices, including sherbet and sorbet (03.0): | 2.00000 | 10.00000 |
Processed fruit (04.1): | 1.00000 | 5.00000 |
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | 5.00000 | 20.00000 |
Confectionery (05.0): | 20.00000 | 100.00000 |
Chewing gum (05.0): | - | - |
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 1.00000 | 5.00000 |
Bakery wares (07.0): | 5.00000 | 20.00000 |
Meat and meat products, including poultry and game (08.0): | 1.00000 | 5.00000 |
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 1.00000 | 5.00000 |
Eggs and egg products (10.0): | 1.00000 | 5.00000 |
Sweeteners, including honey (11.0): | 1.00000 | 5.00000 |
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 5.00000 | 20.00000 |
Foodstuffs intended for particular nutritional uses (13.0): | - | - |
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 1.00000 | 5.00000 |
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 1.00000 | 5.00000 |
Ready-to-eat savouries (15.0): | 1.00000 | 5.00000 |
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 1.00000 | 5.00000 |
Safety References:
Flavor & Extract Manufacturers Association (FEMA) reference(s): |
The FEMA GRAS assessment of alicyclic substances used as flavor ingredients. View pdf |
European Food Safety Athority(EFSA): | Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
European Food Safety Authority (EFSA) reference(s): |
Scientific Opinion on Flavouring Group Evaluation 208 Revision 1 (FGE.208Rev1): Consideration of genotoxicity data on representatives for 10 alicyclic aldehydes with the a,ß-unsaturation in ring / side-chain and precursors from chemical subgroup 2.2 of View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 208 Revision 2 (FGE.208Rev2): Consideration of genotoxicity data on alicyclic aldehydes with a,ß-unsaturation in ring/side-chain and precursors from chemical subgroup 2.2 of FGE.19 View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 73,
Revision 4 (FGE.73Rev4): consideration of alicyclic alcohols,
aldehydes, acids and related esters evaluated by JECFA
(59th and 63rd meeting) structurally related to primary
saturated or unsaturated alicyclic alcohols, aldehydes,
acids and esters evaluated by EFSA in FGE.12Rev5 View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 208 Revision 3 (FGE.208Rev3): consideration of genotoxicity data on alicyclic aldehydes with a,ß-unsaturation in ring/side-chain and precursors from chemical subgroup 2.2 of FGE.19 View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 73, Revision 5 (FGE.73Rev5): consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th, 63rd and 86th meeting) and structurally related to substances evaluated in FGE.12Rev5 View page or View pdf |
EPI System: | View |
AIDS Citations: | Search |
Cancer Citations: | Search |
Toxicology Citations: | Search |
EPA Substance Registry Services (TSCA): | 564-94-3 |
EPA ACToR: | Toxicology Data |
EPA Substance Registry Services (SRS): | Registry |
Laboratory Chemical Safety Summary : | 61130 |
National Institute of Allergy and Infectious Diseases: | Data |
WGK Germany: | 2 |
| 7,7-dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde |
Chemidplus: | 0000564943 |
RTECS: | DT5180000 for cas# 564-94-3 |
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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- |
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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