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beta-pinene

Chemical Structure

General Material Information

Preferred name beta-pinene
Trivial Name β-Pinene
Short Description 2,2,6-trimethyl bicyclo(3.1.1)hept-2-ene
Formula C10 H16
CAS Number 127-91-3
Deleted CAS Number 23089-32-9
FEMA Number 2903
Flavis Number 1.003
ECHA Number 204-872-5
FDA UNII 4MS8VHZ1HJ
Nikkaji Number J2.017F
COE Number 2114
xLogP3-AA 3.10 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1330 beta-pinene
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 127-91-3 ; BETA-PINENE
Synonyms
  • (1)-6,6-dimethyl-2-methylene bicyclo(3.1.1)heptane
  • 7,7-dimethyl-4-methylidenebicyclo[3.1.1]heptane
  • beta- nopinene
  • beta- pinene (refined) (natural)
  • beta- pinene 95 PF
  • beta- pinene 95% natural
  • beta- pinene 97% natural
  • pinene beta
  • pinene beta 95 PF naturel
  • pinene beta pf
  • beta- pinene natural
  • beta- pinene P & F
  • beta- pinene P and F
  • beta- pinene synthetic
  • terbenthene
  • 7,7-dimethyl-4-methylidenebicyclo[3.1.1]heptane
  • Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-
  • 2(10)-Pinene
  • 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane
  • Nopinene
  • Terebenthene
  • β-Pinene
  • Pseudopinen
  • Pseudopinene
  • Nopinen
  • PC 600
  • (±)-2(10)-Pinene
  • (±)-β-Pinene
  • (±)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane
  • PC 600 (pesticide)
  • NSC 21447
  • NSC 406265
  • NSC 59190

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

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Literature & References

7,7-dimethyl-4-methylidenebicyclo[3.1.1]heptane
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:127-91-3
Pubchem (cid):14896
Pubchem (sid):134974399
Flavornet:127-91-3
Pherobase:View
Publications by PubMed
Chemical description and essential oil yield variability of different accessions of Salvia lavandulifolia.
Comparative study on the antioxidant capacity and cholinesterase inhibitory activity of Citrus aurantifolia Swingle, C. aurantium L., and C. bergamia Risso and Poit. peel essential oils.
Antioxidant properties of Thymus vulgaris oil against aflatoxin-induce oxidative stress in male rats.
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
Evaluation of aroma-active compounds in Pontianak orange peel oil ( Citrus nobilis Lour. Var. microcarpa Hassk.) by gas chromatography-olfactometry, aroma reconstitution, and omission test.
Application of biotransformation in flavor and fragrance industry.
Effect of different locations on the chemical composition of essential oils of laurel (Laurus nobilis L.) leaves growing wild in Turkey.
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.
Characterization of volatiles in bullock's heart (Annona reticulata L.) fruit cultivars from Cuba.
The microbial oxidation of (-)-beta-pinene by Botrytis cinerea.
Encapsulation of lemon oil by paste method using beta-cyclodextrin: encapsulation efficiency and profile of oil volatiles.
Characterization of the key aroma compounds in dried fruits of the West African peppertree Xylopia aethiopica (Dunal) A. Rich (Annonaceae) using aroma extract dilution analysis.
Exocrine secretions of wheel bugs (Heteroptera: Reduviidae: Arilus spp.): clarification and chemistry.
Development and assessment of plant-based synthetic odor baits for surveillance and control of malaria vectors.
Antioxidant, antiproliferative and antimicrobial activities of the volatile oil from the wild pepper Piper capense used in Cameroon as a culinary spice.
Assessing the chemotaxis behavior of Physarum polycephalum to a range of simple volatile organic chemicals.
Manuka oil and phoebe oil are attractive baits for Xyleborus glabratus (Coleoptera: Scolytinae), the vector of laurel wilt.
Evaluation of aroma-active compounds in Pontianak orange peel oil ( Citrus nobilis Lour. Var. microcarpa Hassk.) by gas chromatography-olfactometry, aroma reconstitution, and omission test.
Responses of the pollinating wasp Ceratosolen solmsi marchali to odor variation between two floral stages of Ficus hispida.
Analysis of leaf volatiles of Zanthoxylum gillettii used in folk medicine of Cameroon.
Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil.
Defensive secretion components of the host Parastizopus armaticeps as kairomones for the cleptoparasite Eremostibes opacus.
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India.
Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage.
Odor compound detection in male euglossine bees.
Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry.
Exogenous methyl jasmonate induces volatile emissions in cotton plants.
Molecular addition compounds. 18. Borane adducts with hydroxydialkyl sulfide borates for hydroboration. New, essentially odorless, water-soluble sulfide borane acceptors for hydroboration.
Characterization of the key aroma compounds in dried fruits of the West African peppertree Xylopia aethiopica (Dunal) A. Rich (Annonaceae) using aroma extract dilution analysis.
Trigeminal and olfactory chemosensory impact of selected terpenes.
Electroantennographic and coupled gas chromatographic-electroantennographic responses of the mediterranean fruit fly,Ceratitis capitata, to male-produced volatiles and mango odor.

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
FDA Indirect Additives used in Food Contact Substances:View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09882
HMDB (The Human Metabolome Database):HMDB36560
FooDB:FDB015464
Export Tariff Code:2902.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
most commonly available as the l-isomer

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 136.23751831055
Specific gravity @ 25 °C
Pounds per Gallon 7.214 to 7.248
Specific gravity @ 20 °C
Pounds per Gallon 7.198 to 7.264
Refractive Index 1.477 to 1.481 @ 20 °C
Boiling Point 163 to 166°C @ 760 mm Hg
Vapor Pressure 2.93 mmHg @ 25 °C
Flash Point TCC Value 35 °C TCC
logP (o/w) 4.16
Solubility
alcohol Yes
water, 7.061 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Herbal
dry, woody, resinous, pine, hay, green, eucalyptus, camphoreous, cooling, terpenic, fresh, minty, spicy, peppery, nutmeg
Odor strength high , recommend smelling in a 10.00 % solution or less
Substantivity 4 hour(s) at 100.00 %
Luebke, William tgsc, (1985) At 10.00 % in dipropylene glycol. dry woody resinous pine hay green eucalyptus camphoreous
Mosciano, Gerard P&F 25, No. 6, 26, (2000) At 10.00 %. Cooling, woody, piney and turpentine-like with a fresh minty, eucalyptus and camphoraceous note with a spicy peppery and nutmeg nuance
Flavor Type: Pine
pine, terpenic, woody, resinous, minty, camphoreous, balsamic, spicy, fresh
Luebke, William tgsc, (1985) Pine terpenic woody resinous minty camphoreous balsamic spicy
Mosciano, Gerard P&F 25, No. 6, 26, (2000) At 15.00 - 100.00 ppm. Fresh, piney and woody, terpy and resinous with a slight minty, camphoraceous with a spicy nuance
General comment Terpene

Occurrences

Safety Information

Safety information

European information :
Most important hazard(s):
Xn N - Harmful, Dangerous for the environment.
R 10 - Flammable.
R 22 - Harmful if swallowed.
R 36/38 - Irritating to skin and eyes.
R 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
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 37/39 - Wear suitable gloves and eye/face protection.
S 60 - This material and its container must be disposed of as hazardous waste.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
S 62 - If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Flammable liquids (Category 3), H226
Acute toxicity, Oral (Category 4), H302; Acute toxicity, Inhalation (Category 4), H332
Aspiration hazard (Category 1), H304
Skin irritation (Category 2), H315
Skin sensitisation (Category 1), H317
Eye irritation (Category 2A), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
GHS Label elements, including precautionary statements
Pictogramflame.jpghealth-hazard.jpgexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H226 - Flammable liquid and vapour
H302 + H332 - Harmful if swallowed or if inhaled
H304 - May be fatal if swallowed and enters airways
H315 - Causes skin irritation
H317 - May cause an allergic skin reaction
H319 - Causes serious eye irritation
H335 - May cause respiratory irritation
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.
P270 - Do not eat, drink or smoke when using this product.
P271 - Use only outdoors or in a well-ventilated area.
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.
P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P312 - Call a POISON CENTER or doctor/physician if you feel unwell.
P330 - Rinse mouth.
P331 - Do NOT induce vomiting.
P333 + P313 - IF SKIN irritation or rash occurs: Get medical advice/attention.
P337 + P313 - IF eye irritation persists: 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.
P403 + P233 - Store in a well-ventilated place. Keep container tightly closed.
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.
Oral/Parenteral Toxicity:
oral-rat LD50 > 5000 mg/kg
One dose tested.
(Moreno, 1975q)

oral-rat LD50 4700 mg/kg
BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Food and Cosmetics Toxicology. Vol. 16, Pg. 859, 1978.

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-pinene usage levels up to:
12.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 1300.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 759.00 (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. Update in publication number(s): 29
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 48.00000600.00000
beverages(nonalcoholic): 11.0000021.00000
beverages(alcoholic): 10.0000050.00000
breakfast cereal: --
cheese: --
chewing gum: 17.0000023.00000
condiments / relishes: 20.0000040.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 20.0000064.00000
fruit ices: --
gelatins / puddings: 10.0000015.00000
granulated sugar: --
gravies: --
hard candy: 48.00000600.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 9.0000018.00000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 20.0000074.00000
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):

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

Statement on List of Representative Substances for Testing. The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000).
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

Safety and efficacy of eight compounds belonging to chemical group 31 (aliphatic and aromatic hydrocarbons) when used as flavourings for all animal species and categories
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):127-91-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :14896
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2368
WGK Germany:3
7,7-dimethyl-4-methylidenebicyclo[3.1.1]heptane
Chemidplus:0000127913