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(S)-(-)-LIMONENE

(S)-(-)-LIMONENE structure

CAS No:
5989-54-8
Formula:
C10H16
Chemical Name:
(S)-(-)-LIMONENE
Synonyms:
(-)-1,8-p-menthadiene,(S)-(-)-limonene;(S)-(-)-1-methyl-4-(1-methylethenyl)cyclohexene;(s)-(-)-p-mentha-1,8-diene;(s)-(-)-p-mentha-8-diene;(s)-1-methyl-4-(1-methylethenyl)cyclohexene;cyclohexene,1-methyl-4-(1-methylethenyl)-,(S)-;p-Mentha-1,8-diene, (S)-(-)-;p-mentha-1,8-diene,(S)-(-)-
Categories:
Organic Chemistry > Alcohols, Phenols, Phenol Alcohols

Description

Liquid

(4S)-limonene is an optically active form of limonene having (4S)-configuration. It is an enantiomer of a (4R)-limonene.|A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).

(S)-(-)-Limonene is one of the most popular natural occurring cyclic terpenes and its chemical name is D-Limonene. It is a colorless liquid at room temperature with a characteristic lemon-like odor. Although it is insoluble in ether and alcohol, (S)-(-)-Limonene is soluble in water and has a boiling point of 74oC. (S)-(-)-Limonene can be recovered from orange peel from the conversion of press liquor to molasses. It is a major constituent of numerous citrus oils such as lemon, orange, lime, mandarin, and grapefruit, which are fruits from the Rutaceae family.(S)-(-)-Limonene can be obtained by stream distillation of pulp and citrus peels resulting from production of cold-pressed oils and juice or from deterpenation of citrus oils. The compound also occurs in other essences and oils obtained during the processing of citrus juice, including deoiler, essence oil, aroma, and juice oil.

ι-Limonene has a pleasant, lemon-like odor free from camphora ceous and turpentine-like notes. The most important and wide spread terpene; it is known in the d- and ι- optically active forms and in the optically inactive dl-form (known as dipentene); it has been reported found in more than 300 essential oils in amounts ranging from 90 - 95% (lemon, orange, mandarin) to as low as 1% (palmarosa);1 the most widespread form is the d-limonene, followed by the racemic form, and then ι-limonene.

colourless liquid with lemon odour

(S)-(-)-LIMONENE Basic Attributes

Molecular Weight：

136.23

Exact Mass：

136.23

BRN：

2323991

EC Number：

227-815-6

UNII：

47MAJ1Y2NE

TSCA：

TSCA listed

DSSTox ID：

DTXSID6047078

Color/Form：

Clear colorless to pale yellow

HScode：

29029090

Characteristics

XLogP3：

4.57 (LogP)|4.57

Density：

0.844 g/mL at 25 °C(lit.)

Melting Point：

-74°C

Boiling Point：

175-177 °C(lit.)

Refractive Index：

n20/D1.471(lit.)

Water Solubility：

Insoluble

Vapor Pressure：

<3 mm Hg ( 14.4 °C)

Vapor Density：

4.7 (vs air)

Flammability characteristics：

Flammable

Odor：

at 100.00 %. terpene pine herbal peppery

Henrys Law Constant：

3.7×10-4mol/(m3Pa) at 25℃, Schuhfried et al. (2015)

Critical Temperature & Pressure：

Sealed in dry,Store in freezer, under -20°C

Safety Information

Packing level：

III

Hazard category：

wgk germany：

hazard class code：

Xi,N

safety instructions：

24-37-60-61

RTECS Number：

OS8350000

Hazard Statements：

10-38-43-50/53

RIDADR：

UN 2052 3/PG 3

GHS Classification：

|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P321, P331, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 2024 companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, and P501

Exposure Prevention：

Limonene is a racemic form of dand l-limonene. d-Limonene is contained in Citrus species such as citrus, orange, mandarin, and bergamot. l-Limonene is contained in Pinus pinea.

Drug Information

Metabolism/Metabolites：

(-)-limonene has known human metabolites that include Carveol and Perillyl alcohol.

MeSH Entry Terms：

(+)-(R)-4-isopropenyl-1-methylcyclohexene

(S)-(-)-LIMONENE Use and Manufacturing

Uses

(S)-(-)-Limonene is used to inhibit the proliferation of colon cancer cells. It is also used in artificial essential oils in order to produce (+)-carvone. It is an active component of turpentine. Further, it is used in flavorings, fragrances, and cosmetics. It finds application as a solvent and wetting agent. In addition to this it is used to produce resins.

Manufacturing Info：

Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-: ACTIVE

Use Classification：

Food additives -> Flavoring Agents|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]

Food Additive Classes：

Flavoring Agents

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