β-カリオフィレン 化学特性,用途語,生産方法
外観
無色～うすい黄色、液体
定義
本品は、次の化学式で表されるセスキテルペン炭化水素である。
解説
(1R-4E-9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene．C15H24(204.34)．β-カリオフィレンともいう．二環性セスキテルペン．フトモモ科Eugenis caryophyllaのクローブ油のなかにα-カリオフィレンとともに含まれているが，アカマツPinns densifloraやヤマジソMosla japonicaなど，植物界に広く存在している．
"沸点129～130 ℃(1.9 kPa)．[α]D"－9.9°(ベンゼン)．2分子の塩化水素を付加して融点69～70 ℃ の結晶になる．芳香性材料として使われる．α-カリオフィレンはα-フムレンと同じ．
森北出版「化学辞典（第2版）
用途
有機合成原料。
化粧品の成分用途
皮膚コンディショニング剤、香料
天然物の起源
Three isomers (α-, β-, and γ-caryophyllene) are found in nature. The β-isomer is the most frequently encountered
and most abundant. This sesquiterpene hydrocarbon occurs naturally in approximately 60 essential oils, mainly in that of
cloves, from which it was originally isolated. The chemical structure has been thoroughly studied; other studies have been conducted
on the isolation and the dipolar moment, as well as on its oxide. Reported found in lime peel oil, lemon, grapefruit, guava fruit, raspberry,
black currant, carrot, celery seed, cinnamon bark, anise, nutmeg, cumin seed, ginger, pepper, peppermint oil, mace, laurel and
caraway herb.
使用
β-Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.
定義
ChEBI: A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of <greek beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.
製造方法
Isolated from oil of clove stems and separated from eugenol by treating the oil with 7% sodium carbonate solution,
extracting with ether, repeating the carbonate treatment on the concentrated extracts, and finally steam distilling.
空気と水の反応
Insoluble in water.
反応プロフィール
The unsaturated aliphatic hydrocarbons, such as BETA-CARYOPHYLLENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions.
火災危険
BETA-CARYOPHYLLENE is combustible.
安全性プロファイル
A skin irritant.
Combustible liquid. When heated to
decomposition it emits acrid smoke and
irritating fumes.
発がん性
Caryophyllene showed significant
activity as an inducer of the detoxifying enzyme glutathione
S-transferase in the mouse liver and small intestine.
The ability of natural anticarcinogens to induce detoxifying
enzymes has been found to correlate with their activity in the
inhibition of chemical carcinogenesis (253a).
β-カリオフィレン 上流と下流の製品情報
原材料
準備製品