alpha-damascone
1-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-1-one
Identification
| Name | alpha-damascone |
| IUPAC | 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-1-one |
| CAS Number | 43052-87-5 |
| FDA UNII | UP5JTZ982I |
| Molecular Formula | C13 H20 O |
| Molecular Weight | 192.30160000 |
| MDL Number | MFCD00673214 |
| Beilstein | 2208705 |
| CoE Number | 11053 |
Regulatory
| JECFA Food Flavoring | 385 alpha-damascone |
| DG SANTE Food Flavourings | 07.134 alpha-damascone |
| FEMA Number | 3659 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 43052-87-5 ; ALPHA-DAMASCONE |
Physical Properties
| Appearance | pale yellow clear liquid (est) |
| Assay | 98.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.92800 to 0.93800 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.722 to 7.805 |
| Refractive Index | 1.49200 to 1.49900 @ 20.00 °C. |
| Boiling Point | 267.13 °C. @ 760.00 mm Hg (est) |
| Acid Value | 1.00 max. KOH/g |
| Vapor Pressure | 0.008000 mmHg @ 25.00 °C. (est) |
| Flash Point | > 200.00 °F. TCC ( > 93.33 °C. ) |
| logP (o/w) | 3.436 (est) |
| Shelf Life | 12.00 month(s) or longer if stored properly. |
| Storage | store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Soluble in | alcohol |
| Insoluble in | water |
| Stability | alcoholic solution |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | fragrance |
Organoleptic Properties
| Odor Strength | high , |
| Substantivity | 66 hour(s) at 100.00 % |
| Odor Description |
at 1.00 % in dipropylene glycol. Sweet, fruity, floral woody with a green berry nuance
|
| Odor sample from | Ungerer & Company, Inc. |
| Taste Description |
fruity green seedy tropical spicy apple woody at 30.00 ppm.
|
Safety Information
| European information | Most important hazard(s): |
| 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 |
| IFRA Critical Effect | Dermal sensitization |
| fragrance material specification | Should not be used as fragrance ingredients such that the total level in finished cosmetic products exceeds 0.02%, individually or in combination. Based on test data showing sensitising potential for these materials and on evidence of cross-reactivity. (IFRA guidelines) |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| use level in formulae for use in cosmetics | 0.1200 % |
| Dermal Systemic Exposure in Cosmetic Products | 0.0031 mg/kg/day (IFRA, 2002, 2003) |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 7.97 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.40 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 101.3 (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) | - |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | - |
| Edible ices, including sherbet and sorbet (03.0) | - |
| Processed fruit (04.1) | - |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 0.20000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 0.20000 |
| Bakery wares (07.0) | 0.20000 |
| 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) | 0.20000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 0.20000 |
| 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
2-
buten-1-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-
damarose alpha
damascone (alpha)
dihydro floriffone A
1-(2,6,6-
trimethyl-1-cyclohex-2-enyl)but-3-en-1-one
1-(2,6,6-
trimethyl-2-cyclohexen-1-yl)-2-butenone
4-(2,6,6-
trimethyl-2-cyclohexen-1-yl)-but-2-en-4-one
1-(2,6,6-
trimethyl-2-cyclohexenyl)-2-buten-1-one
4-(2,6,6-
trimethyl-2-cyclohexenyl)-2-buten-4-one
4-(2,6,6-
trimethyl-2-cyclohexenyl)-2-butene-4-one
1-(2,6,6-
trimethyl-cyclohex-2-enyl)-but-2-en-1-one
1-(2,6,6-
trimethylcyclohex-2-en-1-yl)but-2-en-1-one
PubMed:
Comparison of aroma active and sulfur volatiles in three fragrant rice cultivars using GC-olfactometry and GC-PFPD.
PubMed:
Influence of triterpenoids present in apple peel on inflammatory gene expression associated with inflammatory bowel disease (IBD).
PubMed:
Analytical and sensory characterization of the aroma of "Langhe D.O.C. Nebbiolo" wines: influence of the prefermentative cold maceration with dry ice.
PubMed:
Characterization of volatiles and aroma-active compounds in honeybush (Cyclopia subternata) by GC-MS and GC-O analysis.
PubMed:
Aromatic aldols and 1,5-diketones as optimized fragrance photocages.
PubMed:
[Isoprenoids and phenylpropanoids from Saussurea deltoidea].
PubMed:
Characterization of the bound volatile extract from baby kiwi (Actinidia arguta).
PubMed:
Structural Analysis of CYP101C1 from Novosphingobium aromaticivorans DSM12444.
PubMed:
Influence of the backbone structure on the release of bioactive volatiles from maleic acid-based polymer conjugates.
PubMed:
Insecticidal potency of novel compounds on multiple insect species of medical and veterinary importance.
PubMed:
Volatile composition screening of Salix spp. nectar honey: benzenecarboxylic acids, norisoprenoids, terpenes, and others.
PubMed:
Identification of 3-hydroxy-beta-damascone and related carotenoid-derived aroma compounds as novel potent inducers of Nrf2-mediated phase 2 response with concomitant anti-inflammatory activity.
PubMed:
Substrate promiscuity of RdCCD1, a carotenoid cleavage oxygenase from Rosa damascena.
PubMed:
[Retention of components in a mixture of volatile organic substances by maltodextrins].
PubMed:
Synthetic applications of enantioselective protonation and case study for (S)-alpha-damascone.
PubMed:
Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis.
PubMed:
Fragrance material review on cis-beta-damascone.
PubMed:
Fragrance material review on gamma-damascone.
PubMed:
Fragrance material review on delta-damascone.
PubMed:
Fragrance material review on alpha-damascone.
PubMed:
Fragrance material review on trans-beta-damascone.
PubMed:
Fragrance material review on cis-alpha-damascone.
PubMed:
Fragrance material review on trans,trans-delta-damascone.
PubMed:
[Investigation of the pyrolysis behavior of 4-oxo-beta-damascone by on-line pyrolysis gas chromatography-mass spectrometry].
PubMed:
Glycosidically bound volatiles and flavor precursors in Laurus nobilis L.
PubMed:
A simple and efficient highly enantioselective synthesis of alpha-ionone and alpha-damascone.
PubMed:
A novel biomimetic route to the 3-acyl-5-hydroxy-3-pyrrolin-2-one and 3-acyl-3,4-epoxy-5-hydroxypyrrolidin-2-one ring systems.
PubMed:
Investigation of bound aroma constituents of yellow-fleshed nectarines (Prunus persica L. Cv. Springbright). changes in bound aroma profile during maturation.
PubMed:
Aroma composition of Vitis vinifera Cv. tannat: the typical red wine from Uruguay.
PubMed:
Identification of (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-beta-D-glucopyranosides as damascenone progenitors in the flowers of Rosa damascena Mill.
PubMed:
Principles and methodology for identification of fragrance allergens in consumer products.
PubMed:
Character impact odorants of the apple cultivars Elstar and Cox Orange.
PubMed:
Volatile compounds released by enzymatic hydrolysis of glycoconjugates of leaves and grape berries from Vitis vinifera Muscat of Alexandria and Shiraz cultivars.
PubMed:
Acid-catalyzed hydrolysis of alcohols and their beta-D-glucopyranosides.
PubMed:
Identification of potent odorants in Japanese green tea (Sen-cha).
PubMed:
C(13)-Norisoprenoid glucoconjugates from lulo (Solanum quitoense L.) leaves.
PubMed:
Bioconversion of alpha-Damascone by Botrytis cinerea.
PubMed:
Progress in synthesis of sensory important trace components of essential oils and natural flavours.