rac-(3R*)-3,7-ジメチル-6-オクテン-1-オール

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Warning

• 危険有害性情報

  H315：皮膚刺激

  H317：アレルギー性皮膚反応を起こすおそれ

• 注意書き

  P261：粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。

  P264：取扱い後は皮膚をよく洗うこと。

  P264：取扱い後は手や顔をよく洗うこと。

  P272：汚染された作業衣は作業場から出さないこと。

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

  P302+P352：皮膚に付着した場合：多量の水と石鹸で洗うこと。

  P321：特別な処置が必要である（このラベルの．．． を見よ）。

  P332+P313：皮膚刺激が生じた場合：医師の診断/手当てを受けるこ と。

  P333+P313：皮膚刺激または発疹が生じた場合：医師の診断/手当てを 受けること。

  P362：汚染された衣類を脱ぎ、再使用す場合には洗濯をすること。

  P363：汚染された衣類を再使用す場合には洗濯をすること。

  P501：内容物/容器を．．．に廃棄すること。

rac-(3R*)-3,7-ジメチル-6-オクテン-1-オール 化学特性,用途語,生産方法

• 定義

  本品は、次の化学式で表されるテルペンアルコールである。

• 化粧品の成分用途

  香料

• 化学的特性

  The enantiomers (3R)-(+)-citronellol and (3S)-(?)-citronellol occur in many essential oils.
  (?)-Citronellol isolated from natural sources is often named rhodinol. At present, the name rhodinol is also used for the isopropenyl isomer α-citronellol or a mixture of the two isomers.
  In many natural products, citronellol occurs as a mixture of its two enantiomers; the pure (+) or (?) formis seldom found. (?)-Citronellol is the predominant enantiomer in geranium and rose oils, both of whichmay contain up to 50% citronellols. Citronellol is a colorless liquid with a sweet rose-like odor. The odor of (?)- citronellol is more delicate than that of (+)-citronellol.
  Citronellol undergoes the typical reactions of primary alcohols. Compared with geraniol, which contains one more double bond, citronellol is relatively stable. Citronellol is converted into citronellal by dehydrogenation or oxidation; hydrogenation yields 3,7-dimethyloctan-l-ol. Citronellyl esters are easily prepared by esterification with acid anhydrides.

• 製造方法

  (?)-Citronellol is still obtained mainly from geranium oil by saponification followed by fractional distillation (“rhodinol”). Although of high odor quality, this grade does not possess the true (?)-citronellol odor due to impurities. Much larger quantities of (+)-citronellol and racemic citronellol are used and are prepared by partial or total synthesis.
  1) Synthesis from citronellal: Citronellal can be hydrogenated to citronellol by the use of special catalysts and/or special hydrogenation techniques, for example, [122]. The citronellal that is used as the starting material may originate from synthetic production or from isolation of essential oils. Citronellal from citronella oil yields (+)-citronellol; the corresponding material from citronellal from Eucalyptus citriodora oil is racemic. Pure (+)-citronellol is also obtained from (+)-citronellal, which is produced as an intermediate of (?)-menthol. By this asymmetric technology, pure (?)-citronellal and, therefore, pure (?)-citronellol are also available.
  2) Synthesis of racemic or slightly dextrorotatory citronellol from geraniol fractions of essential oils: This citronellol is produced by catalytic hydrogenation of saponified geraniol fractions (also containing (+)- citronellol) obtained from Java citronella oil, followed by fractional distillation. Selective hydrogenation of the double bond in the 2-position of geraniol in geraniol–citronellol mixtures isolated from essential oils can be achieved by using Raney cobalt as a catalyst; overhydrogenation to 3,7-dimethyloctan-l-ol can be largely avoided by this method.
  3) Synthesis of racemic citronellol from synthetic geraniol, nerol, or citral: A considerable amount of commercial synthetic racemic citronellol is produced by partial hydrogenation of synthetic geraniol and/or nerol. Another starting material is citral, which can be hydrogenated, for example, in the presence of a catalyst system consisting of transition metals and amines.
  4) Preparation of (?)-citronellol from optically active pinenes: (+)-cis-Pinane is readily synthesized by hydrogenation of (+)-α-pinene or (+)-β-pinene and is then pyrolyzed to give (+)-3,7-dimethyl-1,6-octadiene. This compound can be converted into (?)-citronellol (97% purity) by reaction with triisobutylaluminumor diisobutylaluminumhydride, followed by air oxidation and hydrolysis of the resulting aluminum alcoholate.

• 接触アレルゲン

  L-Citronellol is a constituent of rose and geranium oils. d-Citronellol occurs in Ceylon and Java citronella oils. As a fragrance allergen, citronellol has to be mentioned by name in cosmetics within the EU.

rac-(3R*)-3,7-ジメチル-6-オクテン-1-オール 生産企業

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