Terpineol

α-terpineol
(S)-(-) a body
IUPAC name	p-menth-1-en-8-ol (I derive it from allowable specific epithet) 2-(4-methyl cyclohex-3-エニル) propan-2-ol (systematic name)
Another name	ターピネオール
Molecular formula	C10H18O
Molecular weight	154.25
CAS registration number	[10482-56-1] (S) -(-) a body [7785-53-7] (R) -(+) body [98-55-5] Racemic body [8000-41-7] α, β, γ mixture
Melting point	31-35 degrees Celsius
The boiling point	217-218 degrees Celsius
SMILES	CC1=CCC(C(C)(O)C)CC1

Terpineol (terpineol) is provided from cajuput (cajuput oil), pine oil (pine oil), petitgrain oil (petitgrain oil) with a kind of the naturally occurring monoterpene alcohol [¹]. It is an ingredient of the essential oil of the plant of a laurel, a rosemary, an anise, マジョラム and the Salvia glabrescens genus, the juniper genus and the turpentine. Around 9,600ppm is included in 500ppm, the seed of the nutmeg to Termeric essential oil.

Having the sweet smell similar to the lilac, I am used as an additive to fragrance and cosmetics, soap.

Four kinds of isomers, α, β, γ varying in a hydroxy group and a position of the double bond, δ-terpineol are known. The normal exists as these mixtures, but the chief ingredient is α-terpineol, and the case such as merely terpineol points at this. α-terpineol is isolated from pine oil. Pulegol and piperitol are known as other regioisomeric compounds having double bond and a hydroxy group on the menthane frame one by one.

• 

  α-terpineol

• 

  β-terpineol

• 

  γ-terpineol

• 

  δ-terpineol

Table of contents

Production

I exist, but am made naturally by hydrolyzing α-pinene provided more easily industrially. This reaction is known from the 19th century [²].

 

I am provided by letting you cyclize geraniol or nerol.

The following reactions are known as a manufacturing process of the racemic bodies. I let isoprene make methyl ester and Diels-Alder reaction of acrylic acid, and terpineol is provided when I trigger methyl magnesium bromide (CH₃MgBr) which is kind of the Grignard reagent to a formed cyclohexene derivative [³].

 

As raw materials, using d- limonene, is (R) -(+) -A method to compose α-terpineol selectively is reported [⁴].

 

At first I react limonene with trifluoro acetic acid and get the addition of the マルコフニコフ type. I give terpineol when I hydrolyze formed trifluoro ester acetate with sodium hydroxide. In this reaction, β-terpineol and γ-terpineol by-produce it, and selectivity of the α-isomer is 76%.

Allied law

• I am appointed with dangerous materials (the fourth kind flammable liquid, third oil non-solution liquid) by the Fire Services Act

References

1. ^ Merck Index, 11th Edition, 9103.
2. ^ Bedoukian, P. Z. (1967). "Terpineol" in Perfumery and Flavoring Synthetics. Amsterdam: Elsevier, pp. 328–343.
3. ^ Inukai, T.; Kasai, M. (1965). "Diels-Alder reactions of acrylic acid derivatives catalyzed by aluminum chloride." J. Org. Chem. 30: 3567–3569. doi: 10.1021/jo01021a508.
4. ^ Yuasa, Y.; Yuasa, Y. (2006). "A practical synthesis of d-α-terpineol via Markovnikov addition of d-limonene using trifluoroacetic acid." Org. Process Res. Dev. 10: 1231–1232. doi: 10.1021/op068012d.

Allied item

• Pulegol
• Piperitol
• Thioterpineol

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