酢酸リナリル

酢酸リナリル · 酢酸(S)-1,5-ジメチル-1-ビニル-4-ヘキセニル · 酢酸1-メチル-1-(4-メチル-3-ペンテニル)アリル · ベルガミオール · ベルガモットミントオイル · 3,7-ジメチル-1,6-オクタジエン-3-オールアセタート · ベルガモール · リナロールアセタート

https://huagongshe.com/ja/chemical/8294

識別子と物理属性

CAS No.	115-95-7
分子式	C12H20O2
平均分子量	196.29 g/mol
単同位体質量	196.14632988 g/mol
SMILES	C=CC(C)(CCC=C(C)C)OC(C)=O
InChIKey	UWKAYLJWKGQEPM-UHFFFAOYSA-N
PubChem CID	8294
ChEMBL	CHEMBL502773
ChEBI	CHEBI:78333
EC No.	204-116-4
DTXSID	DTXSID7026946
現地名	酢酸リナリル

化学・物理的性質

XLogP	3.3
極性表面積	26.3
水素結合供与体数	0
水素結合受容体数	2
回転可能結合数	6
重原子数	14
形式電荷	0
複雑度	237
物質分類	Biological Agents -> Plant Oils and Extracts
化粧品	Cosmetics ingredient -> FlavorFragranceMasking
香料	Fragrance Ingredient (Linalyl acetate) -> IFRA transparency List
LogP（分配係数）	log Kow = 3.93
臭い	...floral-fruity odor, reminiscent of bergamot and it also has some pear characterBergamot-lavender odorSweet, floral-fruity odor recalling Bergamot and Pear.100.00%で。スイートグリーンシトラスベルガモットラベンダーウッディ
味	Persistent sweet, acrid tasteSweet, fruity, pear-like with a faintly floral note
食品添加物	FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
密度	0.895 g/cu cm at 20 °CRelative density (water = 1): 0.90.895-0.9140.901 g/mL at 25 °C(lit.)
香味料	EU Flavoring substances
Viscosity	2.4 mm²/s at 23 °C
Color/Form	Clear, colorless, oily liquid
溶解度	Insoluble in waterMiscible with ethanol, etherSoluble in alcohol, ether, diethyl phthalate, benzyl benzoate, mineral oil, fixed oilsslightly soluble in propylene glycolinsoluble in glycerol.Solubility in water: poorinsoluble in glycerol and watermiscible with alcohol and fixed oils1 ml in 5 ml 70% alcohol (in ethanol)クロロホルム（微量）、メタノール（微量）499.8mg/L(25℃)
融点	85°C
沸点	220 °C(lit.)
蒸気密度	6.8 (vs air)
蒸気圧	0.1 mm Hg ( 20 °C)
屈折率	n20/D 1.453(lit.)
FEMA	2636 \| LINALYL ACETATE
引火点	194 °F
貯蔵条件	-20°C
外観・状態	液体
色	無色透明
においのタイプ	ハーブ
由来生物	synthetic
JECFA Number	359
Merck	14,5496
BRN	1724500
ヘンリー定数	1.8×10-2 mol/(m3Pa) at 25℃, Dupeux et al. (2022)
主な用途	洗浄剤化粧品フレーバーそして香料食品および飲料パーソナルケア
化粧品成分の機能	香料
InChI	1S/C12H20O2/c1-6-12(5,14-11(4)13)9-7-8-10(2)3/h6,8H,1,7,9H2,2-5H3
InChIKey	UWKAYLJWKGQEPM-LBPRGKRZSA-N
SMILES	C\C(C)=C\CCC(C)(OC(C)=O)C=C
LogP（分配係数）	3.9 at 25℃
CAS データベース	115-95-7(CAS DataBase Reference)
NISTの化学物質情報	1,6-Octadien-3-ol, 3,7-dimethyl-, acetate(115-95-7)
EPAの化学物質情報	Linalyl acetate (115-95-7)

化学的特性

Linalyl Acetate occurs as its isomer as the main component of lavender oil (30–60%, depending on the origin of the oil), of lavandin oil (25–50%, depending on the species), and of bergamot oil (30–45%). It has also been found in clary sage oil (up to 75%) and in a small amount in many other essential oils. Racemic linalyl acetate is a colorless liquid with a distinct bergamot–lavender odor. Linalyl acetate is used extensively in perfumery. It is an excellent fragrance material for, among others, bergamot, lilac, lavender, linden, neroli, ylang-ylang, and fantasy notes (particularly chypre). Smaller amounts are used in other citrus products. Since linalyl acetate is fairly stable toward alkali, it can also be employed in soaps and detergents.

化学性质

ベルガモット様，ペア様

安全性と法規制

GHS 分類	This chemical does not meet GHS hazard criteria for 13.5% (316 of 2347) of reports.WarningH315 (85.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2347 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報	Chemical: 1,6-Octadien-3-ol, 3,7-dimethyl-, acetateHazard Traits - Fragrance Allergen1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate 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: 11-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14484Linalyl acetate: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報	IMAP assessments - Simple esters of linalool: Human health tier II assessment
火災危険	Combustible. Above 85 °C explosive vapour/air mixtures may be formed.
火災の可能性	Combustible liquid.Combustible.
有害性の概要	Emergency treatment: Linalool[HSDB] Included in list of established contact allergens in humans[EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] Causes somnolence and ataxia and acts as a general anesthetic in lethal dose studies of rats[RTECS] Safe when used as a flavoring agent in food[JECFA] Hydrolyzed in the GI tract into linalool and acetic acidNot a mutagenNot likely to be a sensitizerLinalool, a hydrolysis product, caused hepatocellular cytoplasmic vacuolisation in 28-day feeding studies of rats[Reference #1] See Linalool.
FDA 要件	Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Linalyl acetate is included on this list.

用途

香料原料(石鹸、化粧品、洗剤)。

用途

花,果実用調合香料, 石けん?化粧品?洗剤用香料

天然物の起源

Reported found in the essential oils of bergamot, lavender, clary sage and lavandin; also identified among the constituents of the essential oils of Salvia officinalis, petitgrain, sassafras, neroli, lemon, Italian lime, jasmine, Mentha citrata, Mentha aquatica, Thymus mastichina, etc; also reported in abundant quantities in the essential oil from flowers, leaves and stems of Tagetes patula, in the distillate from leaves of Citrus aurantifolia from India, and in the essential oil of Mentha arvensis. Also reported found in citrus peel oils and juices, berries, peach, celery, tomato, cinnamon, clove, nutmeg, pepper, thymus, grape wines, avocado, mushroom, marjoram, mango, cardamom, coriander, gin, origanum, lovage, laurel, myrtle leaf, rosemary, sage and mastic gum oil.

使用

Linalyl Acetate ermentative production of medium or short chain length alcohol, esters and/or glucosides by metabolically engineered microorganism.

一般的な説明

Linalyl acetate is a monoterpene ester mainly found in lavandula essential oil. It is used as a flavoring agent in food industries, as well as a preservative additive in cosmetics and fragrances such as soaps, colognes, perfumes, and skin lotions.

製法・合成法

製造方法

Linalyl acetate is synthesized by two methods: 1) Esterification of linalool requires special reaction conditions since it tends to undergo dehydration and cyclization as it is an unsaturated tertiary alcohol. These reactions can be avoided as follows: esterification with ketene in the presence of an acidic esterification catalyst below 30 °C results in the formation of linalyl acetate without any by-products. Esterification can be achieved in good yield, with boiling acetic anhydride, whereby the acetic acid is distilled off as it is formed; a large excess of acetic anhydride must be maintained by continuous addition of anhydride to the still vessel. Highly pure linalyl acetate can be obtained by transesterification of tert-butyl acetate with linalool in the presence of sodium methylate and by continuous removal of the tert-butanol formed in the process. 2) Dehydrolinalool, obtained by ethynylation of 6-methyl-5-hepten-2-one, can be converted into dehydrolinalyl acetatewith acetic anhydride in the presence of an acidic esterification catalyst. Partial hydrogenation of the triple bond to linalyl acetate can be carried out with, for example, palladium catalysts deactivated with lead.