caryophyllene
4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
Identification
| Name | caryophyllene |
| IUPAC | (4Z)-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene |
| CAS Number | 13877-93-5 |
| FDA UNII | Search |
| Molecular Formula | C15 H24 |
| Molecular Weight | 204.35628000 |
| MDL Number | MFCD00075925 |
| Nikkaji Number | J101.611C |
| CoE Number | 2618 |
Regulatory
| FEMA Number | 2252 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
Physical Properties
| Appearance | colorless to pale yellow clear oily liquid (est) |
| Assay | 92.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.89700 to 0.91000 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.464 to 7.572 |
| Refractive Index | 1.49800 to 1.50400 @ 20.00 °C. |
| Optical Rotation | -5.00 to -10.00 |
| Boiling Point | 129.00 to 130.00 °C. @ 14.00 mm Hg, 254.00 to 257.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.013000 mmHg @ 25.00 °C. (est) |
| Flash Point | 205.00 °F. TCC ( 96.11 °C. ) |
| logP (o/w) | 6.777 (est) |
| Soluble in | alcohol |
Organoleptic Properties
| Odor Strength | medium |
| Substantivity | 44 hour(s) at 100.00 % |
| Odor Description |
at 100.00 %. Spicy, woody and terpenic
|
| Taste Description | at 50.00 ppm. |
Safety Information
| European information | Most important hazard(s): |
| Human Experience | 4 % solution: no irritation or sensitization. |
| 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 |
| Recommendation for caryophyllene usage levels up to | 8.0000 % in the fragrance concentrate. |
| 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 | - |
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Zanos Ltd.
Distributor of Speciality Chemicals and Natural Ingredients
Sourcing and supplying quality aroma chemicals and prestige natural ingredients for the flavour and fragrance industry.
Potential Uses
Natural Occurrence
Synonyms
bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-
bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-
.gamma.-
caryophyllene
caryophyllene (natural)
caryophyllene 100% (ex clove bud)
caryophyllene alpha + beta mixture
caryophyllene ex terp
caryophyllene FCC
caryophyllene natural isolate
caryophyllene pure natural
8-
methylene-4,11,11-(trimethyl) bicyclo(7.2.0)undec-4-ene
2-
methylene-6,10,10-trimethyl bicyclo 7.2.0 undec-5-ene
(4Z)-4,11,11-
trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene
4,11,11-
trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
US Patents:
3,965,189 - 1-Acetyl-11-methylene-4,7,7-trimethyl-cycloundeca-4,8-diene
PubMed:
trans-Caryophyllene is a natural agonistic ligand for peroxisome proliferator-activated receptor-α.
US Patents:
Sesquiterpenic derivatives as odor- and taste modifying agents
PubMed:
High-density biosynthetic fuels: the intersection of heterogeneous catalysis and metabolic engineering.
PubMed:
Chemical description and essential oil yield variability of different accessions of Salvia lavandulifolia.
PubMed:
Comparison of volatile compounds with characteristic odor in flowers and leaves of nojigiku (Chrysanthemum japonense).
PubMed:
Use of hydrodistillation and headspace solid-phase microextraction to characterize the volatile composition of different hop cultivars.
PubMed:
Characteristic odor components of essential oil from Scutellaria laeteviolacea.
PubMed:
Volatiles profiling in medicinal licorice roots using steam distillation and solid-phase microextraction (SPME) coupled to chemometrics.
PubMed:
Characterization of aroma compounds in Chinese bayberry (Myrica rubra Sieb. et Zucc.) by gas chromatography mass spectrometry (GC-MS) and olfactometry (GC-O).
PubMed:
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed:
Flavor characterization of sugar-added pennywort (Centella asiatica L.) juices treated with ultra-high pressure and thermal processes.
PubMed:
Characteristic aroma-active compounds of Korean perilla (Perilla frutescens Britton) leaf.
PubMed:
Chemical compositions and antioxidant/antimicrobial activities of various samples prepared from Schinus terebinthifolius leaves cultivated in Egypt.
PubMed:
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
PubMed:
Terpene biosynthesis in glandular trichomes of hop.
PubMed:
Improvement of texture properties and flavor of frozen dough by carrot (Daucus carota) antifreeze protein supplementation.
PubMed:
Volatile constituents in the flowers of Elsholtzia argyi and their variation: a possible utilization of plant resources after phytoremediation.
PubMed:
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.
PubMed:
Volatile constituents from the leaves of Callicarpa japonica Thunb. and their antibacterial activities.
PubMed:
Chemical composition, toxicity and mosquito repellency of Ocimum selloi oil.
PubMed:
Changes of the volatile profile and artifact formation in Daidai (Citrus aurantium) cold-pressed peel oil on storage.
PubMed:
Engineering a mevalonate pathway in Escherichia coli for production of terpenoids.
PubMed:
Characterization of volatiles in Costa Rican guava [Psidium friedrichsthalianum (Berg) Niedenzu] fruit.
PubMed:
Characterization of volatiles in strawberry guava (Psidium cattleianum Sabine) fruit.
PubMed:
Determination of Key Flavor Components in Methylene Chloride Extracts from Processed Grapefruit Juice.
PubMed:
Aroma-active compounds of miniature beefsteakplant (Mosla dianthera Maxim).
PubMed:
Flavor compounds of pine sprout tea and pine needle tea.