Camphene

HCID 6616CAS 79-92-5

基本情報

標準SMILES
C=C1C2CCC(C2)C1(C)C
InChIKey
CRPUJAZIXJMDBK-UHFFFAOYSA-N
分子式
C10H16
平均分子量
136.23 g/mol
単同位体質量
136.12520051

概要

Camphene appears as a colorless to white crystalline solid with an insipid camphor-like odor. Dust and crystals are irritants to the eyes, nose and throat. Emits flammable vapors when heated. Emits acrid smoke and irritating fumes at high temperature. Used for the manufacture of synthetic camphor.

名称と識別子

優先名称
Camphene
IUPAC
2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane
現地名
(±)-カンフェン
英語名
Camphene
分子式
C10H16
分子量
136.23

名称と別名

CAMPHENE79-92-5DL-CampheneComphene2,2-Dimethyl-3-methylenenorbornane2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane3,3-Dimethyl-2-methylenenorbornane3,3-Dimethyl-2-methylenenorcamphaneFEMA No. 2229DTXSID8026488Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-
名称をさらに表示
(±)-カンフェン (約20% トリシクレンを含む)カンフェン2,2-ジメチル-3-メチレンビシクロ[2.2.1]ヘプタン3,3-ジメチル-2-メチレンビシクロ[2.2.1]ヘプタン2,2-ジメチル-3-メチレンノルボルナン2-メチレン-3,3-ジメチルノルボルナン2-メチレン-3,3-ジメチルビシクロ[2.2.1]ヘプタン(±)-カンフェン (約20% トリシクレン含む)カンフェン(光学異性体MIX)カンフェン (トリシクレン混合物)(±)-カンフェン2,2-ジメチル-3-メチリデンビシクロ[2.2.1]ヘプタンオクタクロロカンフェンD,L-カンフェンCAMPHENE 46CAMPHENE 90D,L-CAMPHENECamphene(DOT)2,2-Dimethyl-3-methylene-bicyclo[2.2.1]heptaneFEMA 2229(+/-)-Camphene(±)-Camphene (contains ca. 20% Tricyclene)NA 9011
G3VG94Z26EBicyclo(2.2.1)heptane, 2,2-dimethyl-3-methylene-NSC-41652,2-Dimethyl-3-methylenebicyclo(2.2.1)heptaneCHEBI:3830DTXCID0064883,3-dimethyl-2-methylidenebicyclo[2.2.1]heptane2,2-dimethyl-3-methylidenebicyclo(2.2.1)heptane

データベース識別子

CAS
79-92-5
PubChem CID
6616
DTXSID
DTXSID8026488
ChEMBL
CHEMBL2268550
ChEBI
CHEBI:3830
UNII
G3VG94Z26E
EC Number
201-234-8
Nikkaji
J39.020H

物性

構造計算による物性

XLogP
3.3
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
10

実験および物理化学的性質

Chemical ClassesBiological Agents -> Wood Dusts & Extracts
FragrancesFragrance Ingredient (Camphene) -> IFRA transparency List
LogP · 3 件

log Kow = 4.22

4.1 (calculated)

4.56

Odor · 3 件

Camphoraceous, cooling, piney wood with trephy nuances...citrus and green minty and green spicy notes

Insipid odor

Camphor-like

Taste · 2 件

Camphoraceous taste

Terpene, camphoraceous taste...cooling, minty, with citrus and green spicy nuances

Food AdditivesCOLOR OR COLORING ADJUNCT, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

物理化学的性質

融点
48 · 48-52 °C (lit.)
沸点
159 · 159-160 °C (lit.)
比重(密度)
0.85 g/mL · 0.85 g/mL at 25 °C (lit.)
蒸気圧
3.99 hPa · 3.99 hPa (20 °C)
屈折率
1.4551 · 1.4551
FEMA
2229 · 2229 | CAMPHENE

化学的性質

化学的特性Camphene is a colorless to white crystalline solid, Camphor, or turpentine odor. It may be shipped as a liquid. Freezing/Melting point 5 50C.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 2.3% (48 of 2128) of reports.

Danger

H228 (94.8%): Flammable solid [Danger Flammable solids]

P210, P240, P241, P264+P265, P273, P280, P301+P316, P305+P351+P338, P331, P337+P317, P370+P378, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2128 reports by companies from 36 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危険有害性情報

Regulatory Information · 5 件

Chemical: Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-

Regulation (EC) No 1831/2003 (amended)

Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-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)

Status: Active Update: 18-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14290

Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-: 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 Solid
Fire Hazards · 2 件

Excerpt from ERG Guide 133 [Flammable Solids]:

Flammable. Above 26 °C explosive vapour/air mixtures may be formed.

Fire PotentialCombustible; yields flammable vapors when heated ...
Health HazardsInhalation causes irritation of nose and throat. Contact with eyes or skin causes irritation. (USCG, 1999)

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 133 [Flammable Solids]:

Use water spray, powder, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest.

Rinse skin with plenty of water or shower.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink.

First AidINHALATION: move victim to fresh air; call physician immediately.
Safe StorageProvision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. Fireproof.
Fire Fighting Procedures · 3 件

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Extinguish with dry chemicals, foam or carbon dioxide. Water may be ineffective on fire.

Storage Conditions · 2 件

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place.

Storage temperature: ambient; venting: open.

毒性情報

Body Burden · 1 件

One of eight samples of mother's milk collected from 4 urban/industrial areas in the United States was positive for the presence of camphene(1,2). In a heterogenous, nonsmoking population of 62 subjects, camphene was a common constituent in the expired air of control, diabetic, and prediabetic subjects(3).

Interactions · 4 件

... A combination of camphene and geraniol (CG; 1:1), when pre-administered in rats (10 mg/kg BW), accorded protection against nimesulide hepatotoxicity in vivo, as evident from normalized serum biomarkers and histopathology. mRNA expression and activity of key antioxidant and redox enzymes along with oxidative stress were also normalized due to CG pre-treatment. Downstream effects like decreased mitochondrial swelling, inhibition in release of apoptotic proteins, prevention of mitochondrial depolarization along with reduction in oxidized NAD(P)H and increased mitochondrial electron flow further supported protective action of selected terpenes against nimesulide toxicity. Therefore CG, a combination of natural terpenes prevented nimesulide induced cellular damage and ensuing hepatotoxicity.

Exploration of antioxidants of plant origin and scientific validation of their efficacies has unraveled bioactives from natural sources. In this study, two terpenoids camphene and geraniol were assessed for their cytoprotective and antioxidant potential using t-BHP stressed rat alveolar macrophages. Effect of these test substances along with a known plant derived antioxidant quercetin was seen on cell viability, some oxidative stress markers as well as on mitochondrial membrane potential. Both the test substances geraniol and camphene increased the cell viability significantly as indicated by MTT assay and LDH release assay, during pre-treatment of test compound. Camphene and geraniol showed 29% (P<0.05) and 45% (P<0.05) increase in SOD activity, 28% and 120% (P<0.001) increase in GSH content and restored the mitochondrial membrane potential during pre-treatment as compared to stressed cells. Camphene and geraniol were found to significantly decrease lipid peroxidation, inhibit NO release (83.84% and 64.61%) and ROS generation in the pre-treated cells as compared to stressed cells. The test compounds also showed significant protection against ROS during post-treatment of the test compounds. ...

An ointment containing camphene, menthol, and essential oils was found to have broncholytic effects in animals.

Development of atheromatosis of the aorta in rabbits fed 1 g cholesterol/day for 3 months was considerably inhibited by simultaneous administration of a mixture of terpenes including camphene, injected sc in a dose of 1 mL every other day for 6 weeks and then given orally in doses of 2 mL/day.

Ecotoxicity Values · 5 件

LC50; Species: Cyprinodon variegatus (Sheepshead minnow); Concentration: 1.9 ppm for 96 hr (95% confidence limit 1.6-2.2 ppm) /Conditions of bioassay not specified/

LC50; Species: Cyprinodon variegatus (Sheepshead minnow); Conditions: static; Concentration: 1.8 mg/L for 24 hr, 2 mg/L for 48-72 hr

LC50; Species: Brachydanio rerio (Zebrafish); Conditions: flow through; Concentration: 1.4 mg/L for 24 hr, 1.21 mg/L for 48 hr, 0.94 mg/L for 72 hr, 0.72 mg/L for 96 hr /Camphen 87.6%/

LC50; Species: Brachydanio rerio (Zebrafish); Conditions: static; Concentration: 150 mg/L for 48-96 hr /Technical product/

For more Ecotoxicity Values (Complete) data for CAMPHENE (9 total), please visit the HSDB record page.

Environmental Fate · 4 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1000(SRC), determined from a structure estimation method(2), indicates that camphene is expected to have very low mobility in soil(SRC). Volatilization of camphene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.098 atm-cu m/mole(3) based upon its vapor pressure, 2.5 mm Hg(4), and water solubility, 4.6 mg/L(5). Camphene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.5 mm Hg at 25 °C(4). Utilizing the Japanese MITI test,2% of the Theoretical BOD was reached in 4 weeks indicating that biodegradation is not a fast environmental fate process. However, based on screening studies under aerobic conditions in which aqueous landfill leachate containing camphene was incubated with soil and sludge inocula and demonstrated approximately 80% degradation after 14 to 70 hours, camphene may biodegrade in aerobic soils under certain environmental conditions(6,7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1000(SRC), determined from a structure estimation method(2), indicates that camphene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant estimated as 0.098 atm-cu m/mole(SRC) derived from its vapor pressure, 2.5 mm Hg(4), and water solubility, 4.6 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 hour and 5 days, respectively(SRC). According to a classification scheme(6), a BCF range of 432 to 1,290(7) suggests that bioconcentration in aquatic organisms is high to very high(SRC). Based on screening studies under aerobic conditions in which aqueous landfill leachate containing camphene was incubated with soil and sludge inocula and demonstrated approximately 80% degradation after 14 to 70 hours, camphene may biodegrade under certain environmental conditions(8,9).

AQUATIC FATE: When incubated with seawater macrophytes from Resurrection Bay, AK, camphene, present at 0.24 ng/L in surface seawater samples without algae, was not detected when incubated with surface water and macroalgae, and was present at 0.13 ng/L at a depth of 2 meters(1).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), camphene, which has a vapor pressure of 2.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase camphene 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 0.6 days(SRC), calculated from its rate constant of 5.3X10-11 cu cm/molecule-sec at 25 °C(6). Vapor-phase camphene is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is calculated to be 1 day(SRC) from its rate constant of 1.1X10-11 cu cm/molecule-sec(3). The atmospheric lifetime of camphene, from experimental calculations, for reaction with hydroxyl, ozone and nitrate radicals is estimated to be 2.6 hours, 18 days and 1.7 hours respectively(4). Camphene 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 · 1 件

Camphene was identified as a volatile component of ginger (Zingiber officinale) and lovage (Levisticum officinale)(1). Camphene was detected as a volatile component from chickpea (Cicer arietinum L.) seed(2). Camphene was identified as a volatile constituent of stored and fresh mango at 1.6 and 0.3 ug/g, respectively(3). Camphene was detected (concentration not reported) as a volatile compound in the headspace of frankfurter sausages(4).

Adverse EffectsNeurotoxin - Other CNS neurotoxin

法規制情報

FDA Requirements · 1 件

2,2-Dimethyl-3-methylenenorbornane 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 b) 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.

安全データ

wgk
2
tsca
TSCA listed
rtecs
EX1055000
ridadr
UN 1325 4.1/PG 2
hs_code
2902 19 00
risk_code
11-10-50/53-36

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

Unlike most terpenes, camphene forms a glycol in rabbit. The compound excreted is camphene glycol monoglucuronide, which was isolated as a levorotatory potassium salt. On hydrolysis with acid, the compound breaks up to glucuronic acid and camphene glycol, which itself undergoes further change to camphenilaldehyde.

Camphene is converted by Aspergillus niger into 2-nonene-2,3-dicarboxylic acid anhydride, with formation of diacetone alcohol as an artifact.

Absorption, Distribution and Excretion · 3 件

In one study, 3.6% was eliminated unchanged in expired air within 3 hr following dermal application or iv injection of 0.6 ug/kg body weight (0.05 mL camphene in 2.5 mL 1,2-propanediol) into a young pig. The major portion appeared within 5 minutes and 90% within 30 minutes.

/Camphene/ absorbed through the skin was also partially excreted in expired air, appearing within 20 minutes of the start of a 30-minute full bath containing 150 mL pine bath oil ...in 450 L water, and was still detectable 1 day after the bath, although inhalation of volatiles from the bath was prevented. A maximal level was reached after 75 min, with 60% exhaled within first 2 hr and a total of 0.67 uL exhaled during the first 5 hr. This study suggested a major route of elimination of unchanged compound in bile with excretion through intestinal tract, followed by glucuronide formation and excretion via kidney.

Camphene is readily absorbed following inhalation, ingestion, or topical application.

Cellular LocationsMembrane

用途と製造

Uses · 6 件

Occurs in many essential oils; [Merck Index] Used as a food additive, flavoring agent, chemical intermediate, camphor substitute, mothproofing tablet, feedstock for polymerized terpene resins, fragrance, and plasticizer for resins and lacquers; [HSDB]

Chemical intermediate for the perfume component, isobornyl acetate, misc specialty aromatics, and the insecticides isobornyl thiocyanoacetate and toxaphene

Essential oils extracted from leaves and fruits of Schinus areira (Anacardiaceae) were tested for their repellent, toxic and feeding deterrent properties against Tribolium castaneum (Coleoptera: Tenebrionidae) larvae and adults. A topical application assay was employed for the contact toxicity study and filter paper impregnation for the fumigant assay. A treated diet was also used to evaluate the repellent activity and a flour disk bioassay for the feeding deterrent action and nutritional index alteration. The essential oil of the leaves contained mainly monoterpenoids, with alpha-phellandrene, 3-carene and camphene predominant, whereas that from the fruits contained mainly alpha-phellandrene, 3-carene and beta-myrcene. The leaf essential oil showed repellent effects, whereas that from the fruit was an attractant. Both oils produced mortality against larvae in topical and fumigant bioassays, but fumigant toxicity was not found against adults. Moreover, both essential oils produced some alterations in nutritional index. These results show that the essential oils from S. areira could be applicable to the management of populations of Tribolium castaneum. /Schinus areira oil/

Manufacture of synthetic camphor; camphor substitute.

Used in tablet form for mothproofing

For more Uses (Complete) data for CAMPHENE (8 total), please visit the HSDB record page.

U.S. Production · 6 件

2023: 100,000 - <250,000 lb

(1972) PROBABLY GREATER THAN 1.36X10+6 GRAMS

(1976) PROBABLY GREATER THAN 6.81X10+6 GRAMS

Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene- 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).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Bicyclo

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-. Aggregated National Production Volume: 1 to < 10 million pounds.[US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. Bicyclo

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-. National Production Volume: 500,000 - 1,000,000 lb/yr.[USEPA/Pollution Prevention and Toxics; 2012 Chemical Data Reporting Database. Bicyclo

Consumer UsesEtching agent
Industry UsesIntermediate
Methods of Manufacturing · 4 件

(+)-alpha-Pinene is converted into (+)-bornyl chloride by the action of dry hydrogen chloride in a Wagner-Meerwein rearrangement. Base-catalyzed dehydrohalogenation of the (+)-bornyl chloride gives racemic camphene.

Isomerization of alpha-pinene in the presence of solid acidic mineral catalysts

From pinene by catalytic isomerization or from bornyl chloride by heating with alkali in the presence of abietenesulfonic acid.

By heating pinene hydrochloride with alkalis, aniline, or alkali salts such as sodium acetate.

Formulations/Preparations · 2 件

GRADES OF PURITY: Commercial, 75% or greater

Technical

応用分野 · 6 件

解説C10H16(136.23).二環式モノテルペンの一つ.融点52 ℃,沸点158~160 ℃.[α]D+103.5°(エーテル).d5040.8486.n50D1.4605.d5440.8422.n54D1.4551.エーテル,クロロホルム,シクロヘキサンに可溶,エタノールに難溶,水に不溶.昇華性がある.ショウガ科ガジュツCurcuma zedoariaの精油に含まれている(+)-カンフェンと,多くのクスノキ科の植物の精油に含まれている(-)-カンフェン,および(±)-カンフェンが知られている.二重結合を1個もつ二環式モノテルペン。かすかなショウノウ様の香りのある結晶性の塊。旋光性があり,それぞれの異性体がスギの針葉油,マツ科植物の枝葉油などに含まれている。工業的には,塩化ボルニルをアルカリで脱塩化水素化してつくる.森北出版「化学辞典(第2版)

用途香粧品原料や食品香料,食品添加剤、医薬品および香料などの中間原料

天然物の起源Reported found in carrot, dill, fennel, marjoram, nutmeg, parsley, pepper, tarragon and thyme.

使用Camphene is used in the preparation of fragrances and as a food additive for flavoring.

一般的な説明A colorless to white crystalline solid with an insipid camphor-like odor. Dust and crystals are irritants to the eyes, nose and throat. Emits flammable vapors when heated. Emits acrid smoke and irritating fumes at high temperature. Used for the manufacture of synthetic camphor.

使用用途カンフェンは、天然の樟脳 (しょうのう) のような特徴的な匂いがすることから、主に食品香料や化粧品の原料として使用されています。また、非アルコール系消毒・除菌液や虫除け用香料組成物にも使用されています。 その他、化学合成の中間体としての用途も重要です。合成樟脳である化学物質カンファーの中間体としての役割があります。α-からカンフェンが作られますが、カンフェンからカンファーが作られます。 二環性の特徴的な構造と反応性の高い二重結合を有するため、複雑な構造を持つ化学物質の合成に用いられるケースも多いです。例としては、医薬品や殺虫剤、あるいはエステルに誘導することにより異なる香りの香料を製造する用途が挙げられます。

調製方法

製造方法From pinene by catalytic isomerization or from bornyl chloride by heating with alkali in the presence of abietenesulfonic acid.

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補足説明

定義ChEBI: A monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils.

関連反応

11 件

関連ノート

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