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| 融点 | -15 °C | | 沸点 | 229-230 °C (lit.) | | 比重(密度) | 0.879 g/mL at 20 °C (lit.) | | 蒸気密度 | 5.31 (vs air) | | 蒸気圧 | ~0.2 mm Hg ( 20 °C) | | 屈折率 | n20/D 1.474(lit.) | | FEMA | 2507 | GERANIOL | | 闪点 | 216 °F | | 貯蔵温度 | 2-8°C | | 溶解性 | water: soluble0.1g/L at 25°C | | 外見 | Liquid | | 酸解離定数(Pka) | 14.45±0.10(Predicted) | | 比重 | 0.878～0.885 (20/4℃) | | 色 | Clear colorless to pale yellow | | 臭い (Odor) | at 100.00 %. sweet floral fruity rose waxy citrus | | においのタイプ | floral | | 水溶解度 | PRACTICALLY INSOLUBLE | | JECFA Number | 1223 | | Merck | 14,4403 | | BRN | 1722456 | | 安定性： | Stable. Combustible. Incompatible with strong oxidizing agents. | | InChIKey | GLZPCOQZEFWAFX-JXMROGBWSA-N | | LogP | 2.6 at 25℃ | | CAS データベース | 106-24-1(CAS DataBase Reference) | | NISTの化学物質情報 | 2,6-Octadien-1-ol, 3,7-dimethyl-, (E)-(106-24-1) | | EPAの化学物質情報 | trans-Geraniol (106-24-1) |
| 主な危険性 | Xi | | Rフレーズ | 36/37/38-43-41-36-52/53-38 | | Sフレーズ | 26-36-24/25-36/37-61-36/37/39 | | RIDADR | UN1230 - class 3 - PG 2 - Methanol, solution | | WGK Germany | 1 | | RTECS 番号 | RG5830000 | | Hazard Note | Irritant | | TSCA | Yes | | HSコード | 29052900 | | 有毒物質データの | 106-24-1(Hazardous Substances Data) | | 毒性 | The acute oral LD50 value in rats was reported as 3.6 g/kg (Jenner, Hagan, Taylor, Cook & Fitzhugh, 1964) and as 4.8 g/kg, while the iv UD 50 in rabbits was reported as 50 mg/kg (Yamawkai, 1962). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Moreno, 1972). |
| | ゲラニオール Usage And Synthesis |
| 外観 | 無色～わずかにうすい黄色, 澄明の液体 | | 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。 | | 溶解性 | エタノール、アセトン及びクロロホルムに溶けやすく、水にほとんど溶けない。 | | 解説 | ゲラニオール 化学式 C10H17OH 。非環式モノテルペンに属するアルコール。ゲラニオールはトランス形で，沸点 230℃。シス形はネロールと呼ばれ，沸点 225℃である。いずれも植物精油中に含まれる。ゲラニオールは水に不溶，アルコール，エーテルとは混り合う油状液体で，ばら油，ゼラニウム油，シトロネラ油に主成分として含まれ，ばら香をもつ香料として重要。また，ゲラニルピロリン酸エステルはテルペノイド，カロテノイド，ステロイドなどの生合成中間体と考えられている。 | | 用途 | 有機合成原料、香料材料。 | | 用途 | 合成香料であり, とくにバラ系調合香料,誘引剤 | | 用途 | ゲラニオールローズ香を有する代表的非環式モノテルペンアルコール。パロマローザ油、ゼラニウム油、シトロネラ油など多くの植物精油の主成分であり、ゼラニウム油から得られるアルコールとしてゲラニオールと命名された また、シトラス（レモン、ライムなどの柑橘(かんきつ)類）、ティー、フルーツ、タバコなどのフレーバーにも用いられ、ヨノン、ビタミンEおよびAの製造原料でもある。ゲラニオールの立体構造はtrans(E)-型である。その立体異性体であるネロールの立体構造はcis(Z)-型であり、天然に存在するが、香調が異なり使用量は少ない。 | | 化粧品の成分用途 | 香料 | | 説明 | Geraniol has a characteristic rose-like odor. Geraniol may be prepared
by fractional distillation from those essential oils rich in
geraniol, or synthetically from myrcene; commercial geraniol cannot
be classified according to its alcohol content, as most of the
recurring impurities are alcoholic in nature (nerol, citronellol, tetrahydrogeraniol).
Gas-chromatography techniques may be usefully
employed to determine the geraniol content in a product. | | 化学的特性 | Geraniol occurs in nearly
all terpene-containing essential oils, frequently as an ester. Palmarosa oil contains
70–85% geraniol; geranium oils and rose oils also contain large quantities. Geraniol
is a colorless liquid, with a floral, rose-like odor.
Since geraniol is an acyclic, doubly unsaturated alcohol, it can undergo a number
of reactions, such as rearrangement and cyclization. Rearrangement in the
presence of copper catalysts yields citronellal. In the presence of mineral acids, it
cyclizes to form monocyclic terpene hydrocarbons, cyclogeraniol being obtained
if the hydroxy function is protected. Partial hydrogenation leads to citronellol,
and complete hydrogenation of the double bonds yields 3,7-dimethyloctan-l-ol
(tetrahydrogeraniol). Citral may be obtained from geraniol by oxidation or by
catalytic dehydrogenation. Geranyl esters are prepared by esterification.
Geraniol is one of the most frequently used terpenoid fragrance materials.
It can be used in all floral, rose-like compositions and does not discolor soaps. In
flavor compositions, geraniol is used in small quantities to accentuate citrus notes.
It is an important intermediate in the manufacture of geranyl esters, citronellol,
and citral. | | 化学的特性 | colourless to pale yellow liquid with an odour of roses | | 化学的特性 | Geraniol has a characteristic rose-like odor The physical constants vary for the various commercial products, depending on the total geraniol content; specifc gravity and refractive index may be indicative of the purity of the product Commercial geraniol cannot be classifed according to its alcohol content, as most of the recurring impurities are alcoholic in nature (nerol, citronellol, tetrahydrogeraniol) Gas chromatography techniques may be usefully employed to determine the gera- niol content in a product. | | 天然物の起源 | The presence of geraniol in nature has been reported in more than 160 essential oils: ginger grass, lemongrass, Ceylon and Java citronella, tuberose, oak musk, orris, champaca, ylang-ylang, mace, nutmeg, sassafras, Cayenne Bois-de-Rose, Acacia farnesiana, geramium clary sage, spike, lavandin, lavender, jasmine, coriander, carrot, myrrh, eucalyptus, lime, mandarin petitgrain, bergamot petitgrain, bergamot, lemon, orange and others The essential oils of palmarosa and Cymbopogon winterianus contain the highest levels of geraniol (approx 80 to 95%) Also reported in numerous other sources including apple juice, citrus peel oils and juices, bilberry, cranberry, other berries, guava, papaya, cinnamon, ginger, corn mint oil, mustard, nutmeg, mace, milk, coffee, tea, whiskey, honey, passion fruit, plums, mushrooms, mango, starfruit, cardamom, coriander leaf and seeds, litchi, Ocimum basilicum, myrtle leaf, rosemary, clary sage, Spanish sage and chamomile oil | | 使用 | geraniol is perfuming and with tonic properties. It is a primary constituent in many essential oils, including citronella, lavender, lemongrass, orange flower, and ylang-ylang. | | 使用 | Geraniol was used in field evaluation of synthetic herbivore-induced plant volatiles as attractants to beneficial insects.It was used to evaluate the tumor-suppressive potency of isoprenoids in vitro and in vivo. | | 使用 | Geraniol is used in the synthesis of insect repellant. It is also used in the synthesis of Angelicoin A and Herecinone J, which inhibit collagen-induced platelet aggregation. | | 製造方法 | A convenient route for the production of geraniol and nerol consists
of the hydrogenation of citral, which is used in large quantities as an intermediate
in the synthesis of vitamin A. Large-scale processes have, therefore, been developed
for producing geraniol. Currently, these are far more important than isolation
from essential oils. Nevertheless, some geraniol is still isolated from essential
oils for perfumery purposes.
1) Isolation from essential oils: Geraniol is isolated from citronella oils and from
palmarosa oil. Fractional distillation of, for example, Java citronella oil (if necessary,
after saponification of the esters present) yields a fraction containing
about 60% geraniol, as well as citronellol and sesquiterpenes.
Aproductwith a higher geraniol content and slightly different odor quality for
use in fine fragrances is obtained by fractionating palmarosa oil after saponification
of the geranyl esters.
2) Synthesis from β-pinene: Pyrolysis of β-pinene yields myrcene, which is converted
into a mixture of predominantly geranyl, neryl, and linalyl chloride by
addition of hydrogen chloride in the presence of small amounts of catalyst, for
example, copper(I) chloride and an organic quaternary ammonium salt.
After removal of the catalyst, the mixture is reacted with sodium acetate in
the presence of a nitrogen base (e.g., triethylamine) and converted to geranyl
acetate, neryl acetate, and a small amount of linalyl acetate.
Geraniol is obtained after saponification and fractional distillation of the
resulting alcohols.
3) Synthesis from linalool: A 96% pure synthetic geraniol prepared by isomerization
of linalool has become commercially available. Orthovanadates are used
as catalysts, to give a >90% yield of a geraniol–nerol mixture. Geraniol
of high purity is finally obtained by fractional distillation.
A considerable portion of commercially available geraniol is produced by a
modified process: linalool obtained in a purity of about 65% from α-pinene is
converted into linalyl borates, which rearrange in the presence of vanadates
as catalysts to give geranyl and neryl borates. The alcohols are obtained by
hydrolysis of the esters.
4) Synthesis from citral: Citral has very recently come to be produced petrochemically
in very large quantities, so partial hydrogenation of citral has
become a very economical route for the production of geraniol. A high
selectivity for this reaction can be achieved by the use of special catalysts
[106] or by special reaction techniques. | | 定義 | ChEBI: A monoterpenoid consisting of two prenyl units linked head-to-tail and functionalised with a hydroxy group at its tail end. | | Aroma threshold values | Detection: 4 to 75 ppb. | | Taste threshold values | Taste characteristics at 10 ppm: sweet foral rose, citrus with fruity, waxy nuances. | | 工業的に製造 | 現在では合成品のゲラニオールが主流であり、次の3種のプロセスによって工業的に製造されている。 (1)アセトン・アセチレン法（ロッシュ法） アセトンとアセチレンを出発原料として合成する。工程は長いが、収率がよく、生成物の精製も容易である。 (2)イソプレン法（クラレ法） 石油C5留分から得られるイソプレンを出発原料とし、塩化プレニル、メチルヘプテノン、リナロールを経てゲラニオールを合成する。 (3)α(アルファ)-ピネン法（グリドコGlidco社） テレビン油から大量に得られるα-ピネンを原料としてリナロールを合成し、これを異性化してゲラニオールを合成する。 | | 一般的な説明 | Colorless to pale yellow oily liquid with a sweet rose odor. | | 反応プロフィール | An unsaturated aliphatic hydrocarbon and an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. | | 燃焼性と爆発性 | Non flammable | | 抗がん研究 | Starting from antitumor activity against several cell lines by an arrest occurring atthe G0/G1 cell cycle and ultimately with an increase of apoptosis, this molecule wasfound to interfere with the mevalonic cycle enzyme. Suppression of prenylation ofproteins leads to the inhibition of DNA synthesis, and the suppression of 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) leads to a reduction of the mevalonate pool andthus limits protein isoprenylation. In the same way, a reduction of cholesterol biodisponibilitywas controlled (Pattanayak et al. 2009; Ni et al. 2012; Dahham et al.2016). | | 安全性プロファイル | Poison by intravenous
route. Moderately toxic by ingestion,
subcutaneous, and intramuscular routes. A
severe human skin irritant. Combustible
liquid. When heated to decomposition it
emits acrid smoke and irritating fumes. | | 合成 | By fractional distillation from those essential oils rich in geraniol, or synthetically from myrcene. | | 代謝 | Geraniol is metabolized in the rabbit by ω-oxidation and by reduction of an α β-unsaturated bond (Parke, 1968). The products of geraniol metabolism are 'Hildebrandt acid' and 7-carboxy-3-methylocta-6-enoic acid. The latter acid is optically active (Williams, 1959). | | 純化方法 | Purify geraniol by ascending chromatography or by thin layer chromatography on plates of kieselguhr G with acetone/water/liquid paraffin (130:70:1) as solvent system. Hexane/ethyl acetate (1:4) is also suitable. Also purify it by GLC on a silicone-treated column of Carbowax 20M (10%) on Chromosorb W (60-80 mesh). [Porter Pure Appl Chem 20 499 1969.] Store it in full, tightly sealed containers in the cool and protect from light. It has a pleasant odour. [cf p 681, Beilstein 1 IV 2277.] |
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