alpha-cyclocitral
2,6,6-trimethylcyclohex-2-ene-1-carbaldehyde
Identification
| Name | alpha-cyclocitral |
| IUPAC | 2,6,6-trimethylcyclohex-2-ene-1-carbaldehyde |
| CAS Number | 432-24-6 |
| EINECS | 207-080-8 |
| FDA UNII | 762EWR23N8 |
| Molecular Formula | C10 H16 O |
| Molecular Weight | 152.23672000 |
| Nikkaji Number | J127.247K |
| CoE Number | 10326 |
Regulatory
| DG SANTE Food Flavourings | 05.182 2,6,6-trimethylcyclohex-2-ene-1-carbaldehyde |
Physical Properties
| Appearance | colorless to yellow clear liquid (est) |
| Assay | 99.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.95000 to 0.95700 @ 20.00 °C., 0.95000 to 0.95700 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.914 to 7.972 |
| Pounds per Gallon - est. | 7.905 to 7.963 |
| Refractive Index | 1.47000 to 1.48000 @ 20.00 °C., 1.47600 to 1.48300 @ 20.00 °C. |
| Boiling Point | 196.00 to 197.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.382000 mmHg @ 25.00 °C. (est) |
| Flash Point | 148.00 °F. TCC ( 64.44 °C. ) |
| logP (o/w) | 2.855 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| 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 |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.061 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 2.1 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| Dairy products, excluding products of category 02.0 (01.0) | - |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | - |
| Edible ices, including sherbet and sorbet (03.0) | 0.01000 |
| Processed fruit (04.1) | 0.00500 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 0.00600 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | - |
| Bakery wares (07.0) | - |
| Meat and meat products, including poultry and game (08.0) | - |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | - |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | - |
| Foodstuffs intended for particular nutritional uses (13.0) | - |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 0.00200 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | - |
| Ready-to-eat savouries (15.0) | - |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | - |
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Potential Uses
Natural Occurrence
Synonyms
a-
cyclociral
alpha-
cyclocitral
2-
cyclohexene-1-carboxaldehyde, 2,6,6-trimethyl-
2,6,6-
trimethyl cyclohex-2-ene-1-carbaldehyde
2,6,6-
trimethyl-2-cyclohexene-1-carboxaldehyde
2,6,6-
trimethylcyclohex-2-ene-1-carbaldehyde
2,6,6-
trimethylcyclohex-2-enecarbaldehyde
US Patents:
3,940,499 - Food or flavor containing 2,6,6-trimethyl-1-cyclohexen-1-ylacetaldehyde
PubMed:
Analysis of Five Earthy-Musty Odorants in Environmental Water by HS-SPME/GC-MS.
PubMed:
Characterization of typical taste and odor compounds formed by Microcystis aeruginosa.
PubMed:
Carotenoid oxidation products as stress signals in plants.
PubMed:
Review of stress specific organelles-to-nucleus metabolic signal molecules in plants.
PubMed:
Total synthesis and biological evaluation of an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid.
PubMed:
Off-flavor compounds from decaying cyanobacterial blooms of Lake Taihu.
PubMed:
Lactones 43. New biologically active lactones: β-cyclocitral derivatives.
PubMed:
Loss of plastoglobule kinases ABC1K1 and ABC1K3 causes conditional degreening, modified prenyl-lipids, and recruitment of the jasmonic acid pathway.
PubMed:
Reconsidering the nature and mode of action of metabolite retrograde signals from the chloroplast.
PubMed:
Development of models for predicting the predominant taste and odor compounds in Taihu Lake, China.
PubMed:
Volatile organic compounds derived from 2-keto-acid decarboxylase in Microcystis aeruginosa.
PubMed:
Nonenzymic carotenoid oxidation and photooxidative stress signalling in plants.
PubMed:
Synthesis of CDE molecular fragments related to sendanin mediated by titanocene(III).
PubMed:
Treatment with algae extracts promotes flocculation, and enhances growth and neutral lipid content in Nannochloropsis oculata--a candidate for biofuel production.
PubMed:
Carotenoid oxidation products are stress signals that mediate gene responses to singlet oxygen in plants.
PubMed:
Characterization of intracellular & extracellular algae organic matters (AOM) of Microcystic aeruginosa and formation of AOM-associated disinfection byproducts and odor & taste compounds.
PubMed:
Microwave-assisted purge-and-trap extraction device coupled with gas chromatography and mass spectrometry for the determination of five predominant odors in sediment, fish tissues, and algal cells.
PubMed:
The management of undesirable cyanobacteria blooms in channel catfish ponds using a constructed wetland: Contribution to the control of off-flavor occurrences.
PubMed:
Degradation and formation of wood odorant β-cyclocitral during permanganate oxidation.
PubMed:
Simultaneous determination of eight common odors in natural water body using automatic purge and trap coupled to gas chromatography with mass spectrometry.
PubMed:
Solid-phase extraction and GC-MS analysis of potentially genotoxic cleavage products of β-carotene in primary cell cultures.
PubMed:
β-cyclocitral, a grazer defence signal unique to the cyanobacterium Microcystis.
PubMed:
A systematic study on spatial and seasonal patterns of eight taste and odor compounds with relation to various biotic and abiotic parameters in Gonghu Bay of Lake Taihu, China.
PubMed:
Kinetics of cell lysis for Microcystis aeruginosa and Nitzschia palea in the exposure to β-cyclocitral.
PubMed:
Analytical aspects of cyanobacterial volatile organic compounds for investigation of their production behavior.
PubMed:
Carotenoid content impacts flavor acceptability in tomato (Solanum lycopersicum).
PubMed:
{beta}-Apocarotenoids do not significantly activate retinoic acid receptors {alpha} or {beta}.
PubMed:
Blue color formation of cyanobacteria with beta-cyclocitral.
PubMed:
Disinfection by-products from halogenation of aqueous solutions of terpenoids.
PubMed:
Metabolite and target transcript analyses during Crocus sativus stigma development.
PubMed:
A very efficient route toward the 4a-methyltetrahydrofluorene skeleton: short synthesis of (+/-)-dichroanone and (+/-)-taiwaniaquinone H.
PubMed:
Occurrence of dissolved and particle-bound taste and odor compounds in Swiss lake waters.
PubMed:
[Ozonation of odorous organic compounds in eutrophic water].
PubMed:
The degradation of (all-E)-beta-carotene by cigarette smoke.
PubMed:
Global sensitivity analysis for model-based prediction of oxidative micropollutant transformation during drinking water treatment.
PubMed:
Lysis of cyanobacteria with volatile organic compounds.
PubMed:
Synthesis, antimicrobial and antineoplastic activities for agelasine and agelasimine analogs with a beta-cyclocitral derived substituent.
PubMed:
Studies on the aroma of maté (Ilex paraguariensis St. Hil.) using headspace solid-phase microextraction.
PubMed:
Annual dynamics and origins of the odorous compounds in the pilot experimental area of Lake Dianchi, China.
PubMed:
Daphnia behavioural responses to taste and odour compounds: ecological significance and application as an inline treatment plant monitoring tool.
PubMed:
Fibrillin influence on plastid ultrastructure and pigment content in tomato fruit.
PubMed:
Oxidation kinetics of selected taste and odor compounds during ozonation of drinking water.
PubMed:
Dunaliella salina microalga pressurized liquid extracts as potential antimicrobials.
PubMed:
Efficient route to 4a-methyltetrahydrofluorenes: a total synthesis of (+/-)-dichroanal B via intramolecular Heck reaction.
PubMed:
Generation of aroma compounds from Ditaxis heterantha by Saccharomyces cerevisiae.
PubMed:
Carotenoid pigmentation affects the volatile composition of tomato and watermelon fruits, as revealed by comparative genetic analyses.
PubMed:
Identification and aroma impact of norisoprenoids in orange juice.
PubMed:
Volatile organic compound (VOC) analysis and sources of limonene, cyclohexanone and straight chain aldehydes in axenic cultures of Calothrix and Plectonema.
PubMed:
Beta-carotene cleavage products after oxidation mediated by hypochlorous acid--a model for neutrophil-derived degradation.
PubMed:
A peroxidase from Lepista irina cleaves beta,beta-carotene to flavor compounds.
PubMed:
Cleavage of beta,beta-carotene to flavor compounds by fungi.
PubMed:
Synthesis of CDE and BCDE molecular fragments of the limonoids havanensin and azadiradione.
PubMed:
Effect of high irradiance and iron on volatile odour compounds in the cyanobacterium Microcystis aeruginosa.
PubMed:
Synthesis of 9E- and 9Z-locked retinoic acid analogs as ligands for RAR and RXR.
PubMed:
Volatile organic chemicals of a shore-dwelling cyanobacterial mat community.
PubMed:
Dynamics of the volatile organic substances associated with cyanobacteria and algae in a eutrophic shallow lake.
PubMed:
Studies on vitamin A and its related compounds. II. Reformatsky reaction of beta-cyclocitral with methyl gamma-bromosenecioate.
PubMed:
THE CONDENSATION OF beta-CYCLOCITRAL WITH DIMETHYLACROLEIN.