Beta-Pinene

HCID 14896CAS 127-91-3

기본 정보

표준 SMILES
C=C1CCC2CC1C2(C)C
InChIKey
WTARULDDTDQWMU-UHFFFAOYSA-N
분자식
C10H16
평균 분자량
136.23 g/mol
단동위원소 질량
136.12520051

개요

Beta-pinene is an isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants. It has a role as a plant metabolite.

이름 및 식별자

우선 이름
Beta-Pinene
IUPAC
6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane

이름 및 동의어

BETA-PINENE127-91-3Nopinene2(10)-PineneTerbentheneTerebenthene6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptanePin-2(10)-enePseudopinenNopinenPINENE, BETA
이름 더 보기
DTXSID7027049RosemarelBicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-DTXCID507049CHEBI:500256,6-Dimethyl-2-methylenebicyclo(3.1.1)heptaneBicyclo(3.1.1)heptane, 6,6-dimethyl-2-methylene-6,6-Dimethyl-2-methylene-bicyclo(3.1.1)heptane

데이터베이스 식별자

CAS
127-91-3
PubChem CID
14896
DTXSID
DTXSID7027049
ChEMBL
CHEMBL501351
ChEBI
CHEBI:50025
EC Number
204-872-5
Nikkaji
J2.017F

물성

구조 계산 물성

XLogP
3.1
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
0
무거운 원자 수
10

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Terpenes
SpringerMaterials PropertiesOptical coefficient
FragrancesFragrance Ingredient (beta-Pinene) -> IFRA transparency List
LogP · 2건

log Kow = 4.16

4.43

Odor · 3건

CHARACTERISTIC TURPENTINE ODOR; DRY, WOODY OR RESINOUS AROMA

PINEY, TURPENTINE-LIKE ODOR

Terpene odor

TastePINEY, TURPENTINE-LIKE TASTE

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 0.1% (3 of 2276) of reports.

Danger

H226 (99.7%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P321, P331, P332+P317, P333+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2276 reports by companies from 38 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

유해성 정보

Regulatory Information · 4건

Chemical: Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-

Regulation (EC) No 1831/2003 (amended)

Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Beta-pinene: Human health tier II assessment
Hazards Summary · 1건

Turpentine and the monoterpenes (alpha-pinene, beta-pinene, 3-carene) are skin and mucous membrane irritants, and in high concentrations, are central nervous system (CNS) depressants. A dermal sensitizer; [ACGIH] A skin and mucous membrane irritant; Absorption of large doses may cause delirium, ataxia, and injury to the kidneys; [HSDB] A skin and mucous membrane irritant; Can be absorbed through skin; May cause kidney damage and CNS effects; [MSDSonline] See Turpentine. See TERPENES.

FDA Requirements · 1건

Beta-Pinene is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Special Reports · 1건

The Flavor and Fragrance High Production Volume Consortia; Revised Robust Summaries for Bicyclic Terpene Hydrocarbons Submitted to the EPA under the HPV Challenge Program. 202 pp. (November 9, 2006). Available from a search of http://www.epa.gov/chemrtk/pubs/summaries/bictrphy/c13610tc.htm as of October 8, 2008

DOT Emergency Guidelines · 5건

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substances may be transported hot. /alpha-Pinene/

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /alpha-Pinene/

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /alpha-Pinene/

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /alpha-Pinene/

For more DOT Emergency Guidelines (Complete) data for BETA-PINENE (8 total), please visit the HSDB record page.

안전 및 보호

Exposure Control and Personal Protection5.0 [ppm]
Fire Fighting Procedures · 3건

EXTINGUISHING MEDIA. Suitable: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. /(-)-Beta-pinene/

FIREFIGHTING. Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes. Specific Hazard(s): Flammable liquid. Emits toxic fumes under fire conditions. Specific Method(s) of Fire Fighting: Use water spray to cool fire-exposed containers. /(-)-Beta-pinene/

If material on fire or involved in fire: If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Pinene/

Storage ConditionsKeep container closed. Keep away from heat, sparks, and open flame. /(-)-Beta pinene/
Cleanup MethodsAccidetntal Release. METHODS FOR CLEANING UP. Cover with dry-lime, sand, or soda ash. Place in covered containers using non-sparking tools and transport outdoors. /(-)-Beta pinene/
Disposal Methods · 2건

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Contact a licensed professional waste disposal service to dispose of this material. Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal, state, and local environmental regulations. /(-)-Beta pinene/

Preventive Measures · 5건

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Do not breathe vapor. Avoid contact with eyes, skin, and clothing. Avoid prolonged or repeated exposure. /(-)-Beta pinene/

Wash thoroughly after handling. Wash contaminated clothing before reuse. /(-)-Beta pinene/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Pinene/

For more Preventive Measures (Complete) data for BETA-PINENE (7 total), please visit the HSDB record page.

독성 정보

InteractionsBeta-pinene vaporized from turpentine had no effect on hexobarbital sleeping time or parathion mortality in male rats, but increased heptachlor mortality and benzpyrene hydroxylation.
Ecotoxicity Values · 5건

LC50; Species: Green algae; Concentration: 1.44 mg/L for 48 hr /Conditions of bioassay not specified in source examined/

LC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static, 20.1 °C, pH 7.90 + or -0.05, oxygen concentration 8.2 mg/mL; Concentration: 1.25 mg/L for 48 hr /99% pure 1S(-)-isover. Measured purity 97%/

LC50; Species: Oncorhynchus mykiss (Rainbow trout, age 1-4 days); Conditions: freshwater, flow through, 10-11 °C, pH 8.2, hardness 100 mg/L CaCO3, dissolved oxygen 90%; Concentration: 1400 ug/L for 60 days /99% purity/

LC50; Species: Oncorhynchus mykiss (Rainbow trout, age 1-7 days); Conditions: freshwater, flow through, 10-11 °C, pH 8.2, hardness 100 mg/L CaCO3, dissolved oxygen 90%; Concentration: 930 ug/L for 60 days (95% confidence interval: 820-1000 ug/L) /99% purity/

LC50; Species: Pimephales promelas (Fathead minnow); Conditions: freshwater, semi-static, 24.2 °C, pH 7.60 + or -0.1, oxygen concentration 6.6 mg/mL; Concentration: 0.50 mg/L for 96 hr /99% pure 1S(-)-isover. Measured purity 97%/

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,400(SRC), determined from a log Kow of 4.16(2) and a regression-derived equation(3), indicates that beta-pinene is expected to have slight mobility in soil(SRC). Volatilization of beta-pinene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.16 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). beta-Pinene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.93 mm Hg(5). Biodegradation data were not available(SRC, 2008). However, by analogy to alpha-pinene which reached 95% of its theoretical BOD using activated sludge in the Japanese MITI test(6), biodegradation may be an important environmental fate process for beta-pinene in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,400(SRC), determined from a log Kow of 4.16(2) and a regression-derived equation(3), indicates that beta-pinene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hours and 5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 340 days if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 320(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). beta-Pinene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2008). However, by analogy to alpha-pinene which reached 95% of its theoretical BOD using activated sludge in the Japanese MITI test(8), biodegradation may be an important environmental fate process for beta-pinene in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), beta-pinene, which has a vapor pressure of 2.93 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase beta-pinene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.9 hours(SRC), calculated from its rate constant of 7.89X10-11 cu cm/molecule-sec at 25 °C(3). The rate constant for the vapor-phase reaction of beta-pinene with ozone has been estimated as 1.2X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). beta-Pinene does not contain chromophores that absorb at wavelengths >290 nm(5) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1건

beta-Pinene was detected in the aromas of 20 out of 26 and 19 out of 63 fresh wild mushrooms by dynamic headspace concentration and solvent extraction, respectively(1). A purge and trap gas chromatogram technique revealed a 0.0015 ppm beta-pinene concentration in fresh grapefruit juice(2). beta-Pinene was identified as one of the flavor compounds in tea derived from fresh pine sprouts or pine needles harvested from Korean red pine trees (Pinus densiflora Sieb. Et Zucc.) in May-June 1995(3). The compound was identified as a volatile odor compound from 30%, 12% and 5% of total emmsions from fat frankfurters at mean concentrations of 3,330, 3,570 and 5,060 relative peak areas (1 ng of bromobenzene = 100), respectively(4).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Average Daily IntakeConsumption: Annual 7833.33 lbs; Individual: 0.006638 mg/kg/day

규제 정보

FDA Requirements · 1건

Beta-Pinene is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

The biotransformation of (+)-, (-)-, and (+-)-alpha-pinenes, (-)-beta-pinene (nopinene), (-)-cis-pinane, (+)-3-carene, (-)-cis-carane, myrcene, and p-cymene in rabbits was investigated. The major metabolites were as follows: (-)-trans-verbenol from (+)-, (-)-, and (+/-)-alpha-pinenes; (-)-10-pinanol and (-)-1-p-menthene-7,8-diol from (-)-beta-pinene; (-)-alpha-terpineol and (-)-trans-sobrerol from (-)-cis-pinane; (-)-m-mentha-4,6-dien-8-ol, 3-caren-9-ol, (-)-3-carene-9-carboxylic acid, and 3-carene-9,10-dicarboxylic acid from (+)-3-carene; carane-9,10-dicarboxylic acid from (-)-cis-carane; and myrcene-3(10)-glycol, myrcene-1,2-glycol, uroterpenol, and p-cymene-9-carboxylic acid from p-cymene. These metabolisms include allylic oxidation, epoxidation, stereoselective gem-dimethyl hydroxylation and its oxidation, cleavage of a conjugated double bond by epoxidation, and regioselective oxidation, some of which are not found usually in chemical reactions, and due to which various new compounds were determined. This biotransformation of the monoterpene hydrocarbons gave some insect pheromones in high yield.

Absorption, Distribution and Excretion · 2건

Pinene is easily absorbed through the pulmonary system, the skin, and the intestine. /Pinene/

Following immersion of young pigs & one human subject for 30 minutes in baths containing 150 mL of a pine-oil mixture (Fichtennadel-Latschenkieferol Kneipp) in 450 L of water, alpha- & beta-pinene & limonene (components of Latschenkieferol) were detected in exhaled air within 20 minutes reaching maximum levels 50-75 minutes after start of the bath & remaining detectable after 1 day.

용도 및 제조

Uses · 6건

Used as a monomer for terpene resins, a substitute for alpha pinene and a chemical intermediate for fragrances and flavorings; [HSDB] A major constituent of turpentine along with alpha-Pinene and 3-Carene; [ACGIH]

Painting (Solvents) [Category: Paint]

MONOMER FOR TERPENE RESINS-EG, FOR HOT MELT ADHESIVES

CHEM INT FOR FRAGRANCES, EG, MYCENE, GERANIOL & LINALOOL

FLAVORING AGENT FOR ICE CREAM & ICES, CANDY & BAKED GOODS

Polyterpene resins, substitute for alpha pinene, intermediate for perfumes and flavorings.

U.S. Production · 5건

2023: 10,000,000 - <25,000,000 lb

(1979) 2.15X10+10 GRAMS

(1981) 2.04X10+10 GRAMS

beta-Pinene is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5458]

Consumer UsesFragrance
Industry UsesIntermediates
Methods of Manufacturing · 5건

Isolated from American terpentine; also by conversion from alpha-pinene

FRACTIONAL DISTILLATION OF TURPENTINE; ISOMERIZATION OF ALPHA-PINENE

Isolation of the d-form from Ferula galbaniflua Boiss. et Buhse, Umbelliferae

Derived from sulfate wood turpentine

beta-Pinene is produced in large quantities by distillation of turpentine oils.

Formulations/PreparationsMost commonly available as the l-isomer

관련 반응

12건

연결된 노트

불러오는 중…