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피난,디데히드로유도체

Pinane

HCID 10129
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
1330-16-1
표준 SMILES
CC1CCC2CC1C2(C)C
InChIKey
XOKSLPVRUOBDEW-UHFFFAOYSA-N
분자식
C10H18
평균 분자량
138.25 g/mol
단동위원소 질량
138.14085057

개요

Pinane is a clear colorless liquid with lint-like particles. Mild odor. (NTP, 1992)

이름 및 식별자

우선 이름
Pinane
IUPAC
2,6,6-trimethylbicyclo[3.1.1]heptane
현지명
피난,디데히드로유도체
영어명
pinane, didehydro derivative
분자식
C10H16
분자량
136.24

이름 및 동의어

Pinane473-55-22,6,6-Trimethylbicyclo[3.1.1]heptaneDIHYDROPINENEBicyclo[3.1.1]heptane, 2,6,6-trimethyl-DTXSID7025922Bicyclo(3.1.1)heptane, 2,6,6-trimethyl-2,6,6-Trimethylbicyclo(3.1.1)heptaneDTXCID705922CHEBI:35710NSC-76674140V20YT81
이름 더 보기
피난,디데히드로유도체pinane, didehydro derivative2,6,6-trimethyl-bicyclo[3.1.1]heptan didehydroderiv.2,6,6-trimethyl-bicyclo[3.1.1]heptan didehydro deriv.Bicyclo[3.1.1]heptane, 2,6,6-trimethyl-, didehydro deriv.
RefChem:1743022,6,6-trimethylbicyclo(3.1.1)heptane;pinane207-467-1Pinane, endo + exocis-Pinane(1S)-(-)-trans-PinaneMFCD00078047CAS-473-55-2

데이터베이스 식별자

CAS
1330-16-1、473-55-2
PubChem CID
10129
DTXSID
DTXSID7025922
ChEMBL
CHEMBL1422299
ChEBI
CHEBI:35710
EC Number
207-467-1
Nikkaji
J9.284C

물성

구조 계산 물성보충 중

XLogP
3.9
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
0
무거운 원자 수
10
형식 전하
0
복잡도
146

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Wood Dusts & Extracts
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
SpringerMaterials PropertiesDensity
FragrancesFragrance Ingredient (Dihydropinene) -> IFRA transparency List
Density · 2건

0.8467 at 70 °F (NTP, 1992) - Less dense than water; will float

0.8467

Color/FormOil
Solubilityless than 1 mg/mL at 68 °F (NTP, 1992)
Flash Point104 °F (NTP, 1992)
Boiling Point · 2건

304 °F at 760 mmHg (NTP, 1992)

169 °C

Melting Point-53 °C
Vapor Density4.8 approximately (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Vapor Pressure · 2건

2 mmHg at 68 °F approximately (NTP, 1992)

5.16 [mmHg]

물리화학적 성질

녹는점
-54.9 °C · -54.9°C
끓는 점
156.25 °C · 156.25°C
밀도
0.858 · 0.8580
굴절률
1.4713 · 1.4713 (estimate)
화장품 원료 기능
향수
LogP
4.239 · 4.239 (est)
EPA
Pinene (1330-16-1)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P273, P280, P301+P316, P303+P361+P353, P331, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 432 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 3건

Chemical: Bicyclo[3.1.1]heptane, 2,6,6-trimethyl-

Bicyclo[3.1.1]heptane, 2,6,6-trimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Bicyclo[3.1.1]heptane, 2,6,6-trimethyl- 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)

Pinane: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
DOT LabelFlammable Liquid
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound include irritation of the skin and eyes. It may cause nausea if inhaled. It may also cause eye damage.
Hazards SummaryEmergency treatment: Turpentine oil; Turpentine oil can cause delirium, seizures, and coma after ingestion; [HSDB] May cause skin and eye irritation; [CAMEO] An irritant; [MSDSonline] See alpha-Pinene. See Turpentine.
Reactive GroupHydrocarbons, Aliphatic Saturated
Reactivity AlertsHighly Flammable
Reactivity ProfilePINANE is incompatible with strong oxidizers. (NTP, 1992)
Flammable LimitsLower flammable limit: 0.7% by volume @ 320 °F (160 °C); Upper flammable limit: 7.2% by volume @ 320 °F (160 °C)
Air and Water ReactionsHighly flammable. Insoluble in water.
NFPA Hazard Classification · 3건

0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.

0 - Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand.

0 - Materials that in themselves are normally stable, even under fire conditions.

안전 및 보호

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid · 1건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1건

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.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Personal Protective Equipment (PPE) · 1건

RECOMMENDED RESPIRATOR: Where the neat test chemical is stored, weighed and diluted, wear an approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)

독성 정보

Ecotoxicity Values · 2건

LC50; Species: Oncorhynchus mykiss (Rainbow trout, larvae); Conditions: freshwater, flow through, 10 °C, hardness 120 mg/L CaCO3; Concentration: 0.0008 ug/L for 60 days /formulated product/

EC50; Species: Daphnia pulex (Water flea, neonate age <24 hr); Conditions: freshwater, static, 20 °C, hardness 160-180 mg/L CaCO3, alkalinity 120-125 mg/L CaCO3, dissolved oxygen 8-9 mg/L; Concentration: 3354 ug/L for 48 hr; Effect: intoxication, immobilization /> or =96% purity/

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a structure estimation method(2), indicates that dihydropinene is expected to have low mobility in soil (SRC). Volatilization of dihydropinene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.35 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dihydropinene is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.2 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2008).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a structure estimation method(2), indicates that dihydropinene 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 0.35 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 3.4 hr and 4.7 days, respectively(SRC). Dihydropinene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5), an estimated BCF of 450(SRC), from an estimated log Kow of 4.4(6) 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). Biodegradation data were not available(SRC, 2008).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dihydropinene, which has an estimated vapor pressure of 2.19 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dihydropinene 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 29 hr(SRC), calculated from its rate constant of 1.34X10-11 cu cm/molecule-sec at 25 °C(3). Dihydropinene does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey ValuesDihydropinene was detected not quantified in Beaufort cheese from the French Alps via GC-MS analysis(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Ecotoxicity Excerpts · 2건

/AQUATIC SPECIES/ Nearly 500 compounds were detected in the tissues of Great Lakes fish as compared to 8 in tissues of hatchery-reared fish. Lethal concentrations for many representative compounds were determined by testing their acute toxicity (48-hr EC50) to Daphnia pulex. However, the population growth and survival of aquatic organisms over longer time intervals are usually affected at concentrations much lower than the EC50 for a specific chemical. To develop a general relationship between acute and chronic concentrations for representative compounds detected in Great Lakes fish full-life-cycle testing /was initiated/ on D. pulex with ... pinane. Growth and fecundity of daphnids was measured in 16-d tests in the laboratory ... Pinane was moderately toxic to D. pulex in acute studies ... Cyclic alkanes, many of which are constituents of crude oil were represented by pinane for which the EC50 was 3.35 mg/L / at which the endpoint was growth and survival/.

/AQUATIC SPECIES/ To evaluate the hazard of organic compounds detected in Great Lakes fish by gas chromatography/mass spectrometry, ... compounds representative of heterocyclic nitrogen compounds, polycyclic aromatic hydrocarbons, and cyclic alkanes and alkenes /were tested/. Sixty-day bioassays on the effects of nicotine, phenanthrene, pinane, and pinene on the behavior, growth, and survival of rainbow trout fry, Oncorhynchus mykiss, were conducted in a large, constant-flow, temperature-controlled water system.

Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dihydropinene can be estimated to be 1,200(SRC). According to a classification scheme(2), this estimated Koc value suggests that dihydropinene is expected to have low mobility in soil.

Natural Pollution SourcesPinane derivatives occur in wood, the leaves of many plants, algae, and insects. Pinane itself ... does not occur naturally ... formed on the hydrogenation of pinane derivatives
Artificial Pollution Sources · 1건

Dihydropinene's production and use as a chemical intermediate for the production of flavor and fragrance chemicals and use in industry for the production of pinane hydroperoxide(1) may result in its release to the environment through various waste streams(SRC).

Environmental Bioconcentration · 1건

An estimated BCF of 450 was calculated for dihydropinene(SRC), using an estimated log Kow of 4.35(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

Volatilization from Water/Soil · 1건

The Henry's Law constant for dihydropinene is estimated as 0.35 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dihydropinene is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3.4 hrs(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4.7 days(SRC). Dihydropinene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Dihydropinene is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.2 mm Hg(SRC), determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of trans-dihydropinene with photochemically-produced hydroxyl radicals has been estimated as 1.34X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 29 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Dihydropinene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Dihydropinene does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 1건

Occupational exposure to dihydropinene may occur through inhalation and dermal contact with this compound at workplaces where dihydropinene is produced or used. Use data suggests that the general population may be exposed to dihyropinene via inhalation of and dermal contact with consumer products containing this compound. (SRC)

안전 데이터

tsca
TSCA listed
기존화학 물질
KE-05-1046

화학 및 산업

약리 정보

Metabolism/Metabolites · 2건

The major metabolite of pinane was alpha-terpineol and minor metabolites were pinan-2-ol and pinan-3-ol.

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.

용도 및 제조

Uses · 5건

Used to make 3,7-dimethyl-1,6-octadiene (perfumery intermediate); [HSDB]

Pinane is used in industry for the production of pinane hydroperoxide. It is also important as an intermediate in the production of 3,7-dimethylocta-1,6-diene, which is used to produce perfumes, such as citronellol, citronellal and hydroxycitronellal.

... an important starting material in the industrial processes used in the fragrance and flavor industry

... use as a polymerization accelerator for rubber

CHEM INT FOR 3,7-DIMETHYL-1,6-OCTADIENE, A PERFUMERY INT

U.S. Production · 5건

2023: <50,000 lb

(1980) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Dihydropinene 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#5493]

Industry UsesIntermediates
Methods of ManufacturingHYDROGENATION OF ALPHA-PINENE, BETA-PINENE OR AN ISOMERIC MIXTURE
Use ClassificationFragrance Ingredients
General Manufacturing Information · 4건

All Other Basic Organic Chemical Manufacturing

Bicyclo[3.1.1]heptane, 2,6,6-trimethyl-: ACTIVE

The oxidation of pinane with air or oxygen gives 2-pinane hydroperoxide or 2-pinanol. In industry, oxidation is carried out in the presence of catalysts.

Pinane derivatives occur in wood, the leaves of many plants, algae, and insects. Pinane itself ... does not occur naturally ... formed on the hydrogenation of pinane derivatives

관련 반응

2건
반응 기록 만들기
HRID 328913 반응식
HRID 328913생성물로uspto-grants-1977_04
HRID 618991 반응식
HRID 618991반응물로uspto-grants-1999_09

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