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General Material Information

Preferred name beta-cyclocitral
Trivial Name β-Cyclocitral
Short Description 2,6,6-trimethyl-1&2-cyclohexen-1-carboxaldehyde
Formula C10 H16 O
CAS Number 432-25-7
FEMA Number 3639
Flavis Number 5.121
ECHA Number 207-081-3
FDA UNII 77Y0U2X29G
Nikkaji Number J127.248I
MDL MFCD00079078
COE Number 11849
xLogP3-AA 2.40 (est)
NMR Predictor External link
JECFA Food Flavoring 979 2,6,6-trimethyl-1&2-cyclohexen-1-carboxaldehyde
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 977045-71-8 ; 2,6,6-TRIMETHYL-1 AND 2-CYCLOHEXEN-1-CARBOXALDEHYDE
Synonyms
  • .beta.- cyclocitral
  • alpha & beta- cyclocitral
  • b- cyclocitral
  • beta- cyclocitral
  • 1-cyclohexene-1-carboxaldehyde, 2,6,6-trimethyl-
  • cyclohexenecarboxaldehyde, 2,6,6-trimethyl-
  • 2,6,6-trimethyl cyclohexene-1-carbaldehyde
  • 2,6,6-trimethyl-1-cyclohexen-1-carboxaldehyde
  • 2,6,6-trimethyl-1-cyclohexene-1-carbaldehyde
  • 2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde
  • 2,6,6-trimethyl-1(2)-cyclohexen-1-carboxaldehyde
  • 2,6,6-trimethyl-1&2-cyclohexen-1-carboxaldehyde
  • 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde
  • 2,6,6-trimethylcyclohexene-1-carbaldehyde
  • 2,6,6-trimethylcyclohexenecarbaldehyde
  • 2,6,6-trimethylcyclohexene-1-carbaldehyde
  • 1-Cyclohexene-1-carboxaldehyde, 2,6,6-trimethyl-
  • 2,6,6-Trimethyl-1-cyclohexene-1-carboxaldehyde
  • β-Cyclocitral
  • 1-Formyl-2,6,6-trimethyl-1-cyclohexene
  • 2,6,6-Trimethyl-1-cyclohexenecarboxaldehyde

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2,6,6-trimethylcyclohexene-1-carbaldehyde
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:432-25-7
Pubchem (cid):9895
Pubchem (sid):134974161
Flavornet:432-25-7
Pherobase:View
Publications by US Patents
3,975,310 - Cycloaliphatic unsaturated ketones as odor- and taste-modifying agents
3,940,499 - Food or flavor containing 2,6,6-trimethyl-1-cyclohexen-1-ylacetaldehyde
Publications by PubMed
Analysis of Five Earthy-Musty Odorants in Environmental Water by HS-SPME/GC-MS.
Characterization of typical taste and odor compounds formed by Microcystis aeruginosa.
Carotenoid oxidation products as stress signals in plants.
Review of stress specific organelles-to-nucleus metabolic signal molecules in plants.
Total synthesis and biological evaluation of an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid.
Off-flavor compounds from decaying cyanobacterial blooms of Lake Taihu.
Lactones 43. New biologically active lactones: β-cyclocitral derivatives.
Loss of plastoglobule kinases ABC1K1 and ABC1K3 causes conditional degreening, modified prenyl-lipids, and recruitment of the jasmonic acid pathway.
Reconsidering the nature and mode of action of metabolite retrograde signals from the chloroplast.
Development of models for predicting the predominant taste and odor compounds in Taihu Lake, China.
Volatile organic compounds derived from 2-keto-acid decarboxylase in Microcystis aeruginosa.
Nonenzymic carotenoid oxidation and photooxidative stress signalling in plants.
Treatment with algae extracts promotes flocculation, and enhances growth and neutral lipid content in Nannochloropsis oculata--a candidate for biofuel production.
Carotenoid oxidation products are stress signals that mediate gene responses to singlet oxygen in plants.
Characterization of intracellular & extracellular algae organic matters (AOM) of Microcystic aeruginosa and formation of AOM-associated disinfection byproducts and odor & taste compounds.
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.
The management of undesirable cyanobacteria blooms in channel catfish ponds using a constructed wetland: Contribution to the control of off-flavor occurrences.
Degradation and formation of wood odorant β-cyclocitral during permanganate oxidation.
Simultaneous determination of eight common odors in natural water body using automatic purge and trap coupled to gas chromatography with mass spectrometry.
β-cyclocitral, a grazer defence signal unique to the cyanobacterium Microcystis.
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.
Kinetics of cell lysis for Microcystis aeruginosa and Nitzschia palea in the exposure to β-cyclocitral.
Analytical aspects of cyanobacterial volatile organic compounds for investigation of their production behavior.
Carotenoid content impacts flavor acceptability in tomato (Solanum lycopersicum).
{beta}-Apocarotenoids do not significantly activate retinoic acid receptors {alpha} or {beta}.
Blue color formation of cyanobacteria with beta-cyclocitral.
Disinfection by-products from halogenation of aqueous solutions of terpenoids.
Metabolite and target transcript analyses during Crocus sativus stigma development.
A very efficient route toward the 4a-methyltetrahydrofluorene skeleton: short synthesis of (+/-)-dichroanone and (+/-)-taiwaniaquinone H.
Occurrence of dissolved and particle-bound taste and odor compounds in Swiss lake waters.
[Ozonation of odorous organic compounds in eutrophic water].
The degradation of (all-E)-beta-carotene by cigarette smoke.
Global sensitivity analysis for model-based prediction of oxidative micropollutant transformation during drinking water treatment.
Lysis of cyanobacteria with volatile organic compounds.
Synthesis, antimicrobial and antineoplastic activities for agelasine and agelasimine analogs with a beta-cyclocitral derived substituent.
Studies on the aroma of maté (Ilex paraguariensis St. Hil.) using headspace solid-phase microextraction.
Annual dynamics and origins of the odorous compounds in the pilot experimental area of Lake Dianchi, China.
Daphnia behavioural responses to taste and odour compounds: ecological significance and application as an inline treatment plant monitoring tool.
Fibrillin influence on plastid ultrastructure and pigment content in tomato fruit.
Dunaliella salina microalga pressurized liquid extracts as potential antimicrobials.
Efficient route to 4a-methyltetrahydrofluorenes: a total synthesis of (+/-)-dichroanal B via intramolecular Heck reaction.
Generation of aroma compounds from Ditaxis heterantha by Saccharomyces cerevisiae.
Carotenoid pigmentation affects the volatile composition of tomato and watermelon fruits, as revealed by comparative genetic analyses.
Identification and aroma impact of norisoprenoids in orange juice.
Volatile organic compound (VOC) analysis and sources of limonene, cyclohexanone and straight chain aldehydes in axenic cultures of Calothrix and Plectonema.
Beta-carotene cleavage products after oxidation mediated by hypochlorous acid--a model for neutrophil-derived degradation.
A peroxidase from Lepista irina cleaves beta,beta-carotene to flavor compounds.
Cleavage of beta,beta-carotene to flavor compounds by fungi.
Effect of high irradiance and iron on volatile odour compounds in the cyanobacterium Microcystis aeruginosa.
Synthesis of 9E- and 9Z-locked retinoic acid analogs as ligands for RAR and RXR.
Volatile organic chemicals of a shore-dwelling cyanobacterial mat community.
Dynamics of the volatile organic substances associated with cyanobacteria and algae in a eutrophic shallow lake.
Studies on vitamin A and its related compounds. II. Reformatsky reaction of beta-cyclocitral with methyl gamma-bromosenecioate.
THE CONDENSATION OF beta-CYCLOCITRAL WITH DIMETHYLACROLEIN.

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
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C20425
HMDB (The Human Metabolome Database):HMDB41011
FooDB:FDB020874
Export Tariff Code:2912.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Specific gravity @ 25 °C
Pounds per Gallon 7.905 to 7.963
Refractive Index 1.476 to 1.483 @ 20 °C
Boiling Point 62 to 63°C @ 3 mm Hg
Boiling Point 211 to 212°C @ 760 mm Hg
Vapor Pressure 0.176 mmHg @ 25 °C
Flash Point TCC Value 76.67 °C TCC
logP (o/w) 3.1 est
Solubility
alcohol Yes
water, 86.14 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Tropical
tropical, saffron, herbal, clean, rose, sweet, tobacco, green, fruity
Odor strength high , recommend smelling in a 10.00 % solution or less
Substantivity 85 hour(s) at 100.00 %
Luebke, William tgsc, (2009) At 10.00 % in dipropylene glycol. tropical saffron herbal clean rose oxide sweet tobacco damascone fruity
Flavor Type: Tropical
tropical, saffron, herbal, tobacco, medicinal, phenolic, leathery, green
Luebke, William tgsc, (2009) Tropical saffron herbal tobacco medicinal phenolic leathery green

Occurrences

Potential Uses

Applications
Odor purposes Agrumen aldehyde, Ajowan, Alpine bouquet, Angelica, Apricot, Arnica flower, Ash mountain ash berry, Basil oil replacer, Bayberry, Bayberry, Calamus oil replacer, Camphor tree bark, Caraway seed, Carrot seed, Celery, Chamomile, Chrysanthemum, Cilantro, Clary sage oil replacer, Coconut tropical coconut, Coriander, Country meadow, Cranberry, Cubeb, Currant bud absolute replacer, Cypress oil replacer, Elder flower, Eucalyptus oil replacer, Forest, Genet, Ginger white ginger, Gingergrass, Gooseberry, Heather, Herbal, Hollyberry, Hop, Hyssop, Ivy, Lavandin, Lavender, Lavender spike lavender, Lovage root, Mango, Marigold, Marjoram, Melissa oil replacer, Myrtle oil replacer, Niaouli, Oregano, Parsley leaf, Passion fruit, Pina colada, Pine forest, Pomegranate, Reseda, Rosemary, Rue, Saffron, Savin, Spruce, Sweet grass, Tansy oil replacer, Tea green tea, Thyme oil white replacer, Valerian, Witch hazel, Woodruff, Wormwood oil replacer, Yerba mate
Flavoring purposes Ajowan, Angelica, Camphor tree bark, Capsicum, Caraway seed, Carrot seed, Chervil, Cilantro, Coriander, Cubeb, Currant bud absolute replacer, Fruit tropical fruit, Gin, Hyssop, Lavender spike lavender, Lovage root, Marigold, Marjoram, Parsley leaf, Rue, Savin, Tansy oil replacer, Tea, Tea black tea, Tea herbal tea, Tea lemon tea, Tropical, Valerian, Yerba mate
Other purposes Blossom tropical blossom, Chewing gum, Confection, Parsnip, Tea china
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
R 26/27/28 - Very toxic by inhalation, in contact with skin and if swallowed.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
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

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 beta-cyclocitral usage levels up to:
2.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.37 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): ND (μg/capita/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: 12
Click here to view publication 12
average usual ppmaverage maximum ppm
baked goods: -0.06000
beverages(nonalcoholic): -0.02000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -0.50000
condiments / relishes: --
confectionery froastings: -0.05000
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: -0.10000
gelatins / puddings: -0.05000
granulated sugar: --
gravies: --
hard candy: -0.10000
imitation dairy: --
instant coffee / tea: --
jams / jellies: -0.05000
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: -0.05000
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

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 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

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):432-25-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9895
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2,6,6-trimethylcyclohexene-1-carbaldehyde
Chemidplus:0000432257