Preferred name | dextro-limonene |
Trivial Name | 1-methyl-4-prop-1-en-2-ylcyclohexene |
Short Description | D-limonene |
Formula | C10 H16 |
CAS Number | 5989-27-5 |
CAS Number | 58555-74-1 |
Deleted CAS Number | 7705-13-7 |
FEMA Number | 2633 |
Flavis Number | 1.045 |
ECHA Number | 227-813-5 |
FDA UNII | GFD7C86Q1W |
Nikkaji Number | J2.532A |
MDL | MFCD00062991 |
COE Number | 491 |
xLogP3-AA | 3.40 (est) |
Bio Activity Summary | External link |
NMR Predictor | External link |
JECFA Food Flavoring | 1326 D-limonene |
FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
FDA Mainterm | 5989-27-5 ; D-LIMONENE |
Synonyms |
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Perfumer & Flavorists | Start search |
EU Patents | Start search |
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NCBI | Start search |
Leffingwell: | Chirality or Article |
1-methyl-4-prop-1-en-2-ylcyclohexene | |
NIST Chemistry WebBook: | Search Inchi |
Canada Domestic Sub. List: | 5989-27-5 |
Pubchem (cid): | 22311 |
Pubchem (sid): | 135017143 |
Flavornet: | 5989-27-5 |
Pherobase: | View |
(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene | |
NIST Chemistry WebBook: | Search Inchi |
Canada Domestic Sub. List: | 58555-74-1 |
Pubchem (cid): | 440917 |
Pubchem (sid): | 135192466 |
(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 |
Golm Metabolome Database: | Search |
UM BBD: | Search |
KEGG (GenomeNet): | C06078 |
HMDB (The Human Metabolome Database): | HMDB04321 |
FooDB: | FDB014297 |
Export Tariff Code: | 2902.19.0050 |
Typical G.C. | |
VCF-Online: | VCF Volatile Compounds in Food |
ChemSpider: | View |
Formulations/Preparations: •equine leg paint contains 1.0% wtvol turpentine: a medium strength solution for use when counterirritant-stimulant action falling between stimulating liniment and blistering ointment is desired. •typical composition from usa southern pine: from 1) gum - 60 to 65% alpha-pinene, 25-35% beta-pinene, and 5-8% other terpenes; 2) wood- 75 to 80% alpha-pinene, 0-2% beta-pinene, 4-8% camphene, and 15-20% other terpenes; 3) sulfate- 60 to 70% alpha-pinene, 20-25% beta-pinene, and 6-12% other terpenes. •turpentine includes mainly c10-terpenes, especially alpha-pinene and beta-pinene, and is typical of the volatile oil portions of various oleoresins. |
Material listed in food chemical codex | Yes |
Molecular weight | 136.23751831055 |
Specific gravity | @ 25 °C |
Pounds per Gallon | 6.973 to 7.015 |
Specific gravity | @ 25 °C |
Pounds per Gallon | 6.965 to 7.031 |
Refractive Index | 1.471 to 1.477 @ 20 °C |
Boiling Point | 175 to 177°C @ 760 mm Hg |
Acid Value | 5 max KOH/g |
Vapor Pressure | 0.198 mmHg @ 25 °C |
Vapor Density | 4.7 |
Flash Point TCC Value | 47.22 °C TCC |
logP (o/w) | 4.57 |
Shelf life | 12 months (or longer if stored properly.) |
Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. store under nitrogen. |
Solubility | |
alcohol | Yes |
fixed oils | Yes |
kerosene | Yes |
paraffin oil | Yes |
water, 13.8 mg/L @ 25 °C (exp) | Yes |
water | No |
propylene glycol | No |
Odor Type: Citrus | |
citrus, orange, fresh, sweet, peely | |
Odor strength | medium |
Substantivity | 4 hour(s) at 100.00 % |
Luebke, William tgsc, (1988) | At 100.00 %. citrus orange fresh sweet |
Mosciano, Gerard P&F 19, No. 3, 51, (1994) | Sweet, citrus and peely |
Flavor Type: Citrus | |
sweet, orange, citrus, terpenic | |
Mosciano, Gerard P&F 19, No. 3, 51, (1994) | At 30.00 ppm. Sweet, orange, citrus and terpy |
Useful in: mint, savory vegetable, savory spices, fruity citrus, fruity red, fruity yellow, fruity tropical, sweet others. | Citrus, fruity, orange, berry flavor, tar-like |
(data available) |
Applications | |
Odor purposes | Banana, Bergamot, Bubble gum, Caraway seed, Celery, Cherry, Citrus, Coffee, Dill weed, Elemi, Evergreen, Floral, Fruit juicy fruit, Grapefruit, Herbal, Lemon, Lime, Lotus, Mandarin, Mint, Neroli, Nutmeg, Orange, Petitgrain lemon petitgrain, Pineapple, Raspberry, Sassafras, Spearmint, Spice, Valerian |
Flavoring purposes | Caraway seed, Carrot, Cola, Dill weed, Grenadine, Petitgrain lemon petitgrain, Valerian |
Other purposes | Erigeron |
Cosmetic purposes | Fragrance, Perfuming agents |
Preferred SDS: View | |
European information : | |
Most important hazard(s): | |
Xi N - Irritant, Dangerous for the environment. | |
R 10 - Flammable. R 36/38 - Irritating to skin and eyes. R 43 - May cause sensitisation by skin contact. R 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R 65 - Harmful: may cause lung damage if swallowed. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. 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 - Wear suitable protective clothing. S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet. | |
Hazards identification | |
Classification of the substance or mixture | |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
Flammable liquids (Category 3), H226 Aspiration hazard (Category 1), H304 Skin irritation (Category 2), H315 Skin sensitisation (Category 1), H317 Acute aquatic toxicity (Category 1), H400 Chronic aquatic toxicity (Category 1), H410 | |
GHS Label elements, including precautionary statements | |
Pictogram | ![]() ![]() ![]() ![]() |
Signal word | Danger |
Hazard statement(s) | |
H226 - Flammable liquid and vapour H304 - May be fatal if swallowed and enters airways H315 - Causes skin irritation H317 - May cause an allergic skin reaction H400 - Very toxic to aquatic life H410 - Very toxic to aquatic life with long lasting effects | |
Precautionary statement(s) | |
P210 - Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233 - Keep container tightly closed. P240 - Ground/bond container and receiving equipment. P241 - Use explosion-proof electrical/ventilating/lighting/…/equipment. P242 - Use only non-sparking tools. P243 - Take precautionary measures against static discharge. P261 - Avoid breathing dust/fume/gas/mist/vapours/spray. P264 - Wash skin thouroughly after handling. P272 - Contaminated work clothing should not be allowed out of the workplace. P273 - Avoid release to the environment. P280 - Wear protective gloves/protective clothing/eye protection/face protection. P301 + P310 - IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P303 + P361 + P353 - IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P331 - Do NOT induce vomiting. P333 + P313 - IF SKIN irritation or rash occurs: Get medical advice/attention. P362 - Take off contaminated clothing and wash before reuse. P370 + P378 - In case of fire: Use dry sand, dry chemical or alcohol-resistant foam for extinction. P391 - Collect spillage. Hazardous to the aquatic environment P403 + P235 - Store in a well-ventilated place. Keep cool. P405 - Store locked up. P501 - Dispose of contents/ container to an approved waste disposal plant. | |
Human Experience: | |
4 % solution: no irritation or sensitization. | |
Oral/Parenteral Toxicity: | |
oral-rat LD50 [sex: M] > 5000 mg/kg Identity of compound not stated as other than code number (Moreno, 1972m) oral-rat LD50 [sex: M,F] M:4400 F:5100 mg/kg Study is on dogs, rats not mentioned in English text. Study in Japanese (Tsuji et al., 1975a) oral-mouse LD50 [sex: M,F] M:5600 F:6600 mg/kg Study is on dogs, mice not mentioned in English text. Study in Japanese (Tsuji et al., 1975a) intraperitoneal-mouse LD50 600 mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 1439, 1974. oral-mouse LD50 5600 mg/kg LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975. intraperitoneal-rat LD50 3600 mg/kg BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975. intravenous-rat LD50 110 mg/kg SKIN AND APPENDAGES (SKIN): HAIR: OTHER LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975. oral-rat LD50 4400 mg/kg SKIN AND APPENDAGES (SKIN): HAIR: OTHER LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975. | |
Dermal Toxicity: | |
skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 13, Pg. 825, 1975. subcutaneous-mouse LD50 3170 mg/kg PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 3, Pg. 73, 1952. skin-mammal (species unspecified) LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 12, Pg. 703, 1974. subcutaneous-rat LDLo 30200 mg/kg LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: EXCITEMENT SKIN AND APPENDAGES (SKIN): HAIR: OTHER Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 387, 1975. | |
Inhalation Toxicity: | |
Not determined |
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 | |||
IFRA Critical Effect: | |||
Dermal sensitization | |||
IFRA Other Specification: | |||
IFRA fragrance material specification: | |||
d-, l-and dl-Limonene and natural products containing substantial amounts of it, should only be used when the level of peroxides is kept to the lowest practical level, for instance by adding antioxidants at the time of production. Such products should have a peroxide value of less than 20 millimoles peroxides per liter, determined according to the FMA method, which can be downloaded from the IFRA website (see Analytical Methods). | |||
View the IFRA Standard | |||
Recommendation for dextro-limonene usage levels up to: | |||
20.0000 % in the fragrance concentrate. | |||
Maximised Survey-derived Daily Intakes (MSDI-EU): | 34000.00 (μg/capita/day) | ||
Maximised Survey-derived Daily Intakes (MSDI-USA): | 12726.00 (μg/capita/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: 3 | |||
Click here to view publication 3 | |||
average usual ppm | average maximum ppm | ||
baked goods: | - | 120.00000 | |
beverages(nonalcoholic): | - | 31.00000 | |
beverages(alcoholic): | - | - | |
breakfast cereal: | - | - | |
cheese: | - | - | |
chewing gum: | - | 2300.00000 | |
condiments / relishes: | - | - | |
confectionery froastings: | - | - | |
egg products: | - | - | |
fats / oils: | - | - | |
fish products: | - | - | |
frozen dairy: | - | 68.00000 | |
fruit ices: | - | 68.00000 | |
gelatins / puddings: | 48.00000 | 400.00000 | |
granulated sugar: | - | - | |
gravies: | - | - | |
hard candy: | - | 49.00000 | |
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: | - | - |
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): |
Flavouring Group Evaluation 25, (FGE.25)[1] - Aliphatic and aromatic hydrocarbons from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
Flavouring Group Evaluation 78 (FGE.78)[1] - Consideration of Aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25 - Scientific Opinion of the Panel on Food Additives,Flavourings, Processing Aids and Materials in Contact with Food (AFC) View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 25Rev1: Aliphatic and aromatic hydrocarbons from chemical group 31 View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 78, Revision 1 (FGE.78Rev1): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25Rev2 View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 25, Revision 2 (FGE.25Rev2): Aliphatic and aromatic hydrocarbons from chemical group 31 View page or View pdf |
Review of substances/agents that have direct beneficial effect on the environment: mode of action and assessment of efficacy View page or View pdf |
Conclusion on the peer review of the pesticide risk assessment of the active substance terpenoid blend QRD-460 View page or View pdf |
Scientific Opinion on the safety and efficacy of aliphatic and aromatic hydrocarbons (chemical group 31) when used as flavourings for all animal species View page or View pdf |
Scientific Opinion on Flavouring Group Evaluation 78, Revision 2 (FGE.78Rev2): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic hydrocarbons evaluated by EFSA in FGE.25Rev3 View page or View pdf |
Outcome of the consultation with Member States, the applicant and EFSA on the pesticide risk assessment for orange oil in light of confirmatory data View page or View pdf |
EPI System: View |
EPA-Iris:IRIS |
NIOSH International Chemical Safety Cards:search |
Chemical Carcinogenesis Research Information System:Search |
AIDS Citations:Search |
Cancer Citations:Search |
Toxicology Citations:Search |
Carcinogenic Potency Database:Search |
EPA Substance Registry Services (TSCA):5989-27-5 |
EPA ACToR:Toxicology Data |
EPA Substance Registry Services (SRS):Registry |
Laboratory Chemical Safety Summary :22311 |
National Institute of Allergy and Infectious Diseases:Data |
SCCNFP:opinion |
WISER:UN 2319 |
WGK Germany:2 |
1-methyl-4-prop-1-en-2-ylcyclohexene |
Chemidplus:0005989275 |
EPA/NOAA CAMEO:hazardous materials |
RTECS:5989-27-5 |
(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene |
Chemidplus:0058555741 |