D-Limonene

D-Limonene
Compound Structure:
Synonyms: (4R)-1-methyl-4-prop-1-en-2-ylcyclohexene; D-Limonene; (+)-Limonene; (+)-(4R)-Limonene; (+)-carvene; (+)-Dipentene; Citrene; (+)-p-Mentha-1,8-diene; (4R)-4-isopropenyl-1-methylcyclohexene; d-p-Mentha-1,8-diene; (+)-4-Isopropenyl-1-methylcyclohexene
Compound ID: NMPC-973
PubChem ID:

440917

Molecular Formula: C10H16
Canonical SMILES: CC1=CCC(CC1)C(=C)C
InChIKey: XMGQYMWWDOXHJM-JTQLQIEISA-N
About the compound:

D-Limonene is a clear, colorless liquid known for its mobile properties and pleasant lemon-like odor. This information was provided by the National Toxicology Program in 1992. (4R)-limonene is an optically active form of limonene that has a (4R)-configuration. It acts as a plant metabolite and is one enantiomer of (4S)-limonene. Limonene is commonly found in cosmetic products due to its appealing fragrance. As the main odor component of citrus fruits, belonging to the Rutaceae family, D-limonene is widely used in food manufacturing and in some medicines. It serves as a flavoring agent to mask the bitter taste of alkaloids and is also employed in perfumery for its fragrant properties. Chemically, limonene is a colorless liquid aliphatic hydrocarbon, classified as a cyclic monoterpene. It is a major component in the volatile oil extracted from citrus fruit peels. The D-isomer of limonene, which is more commonly found in nature, is known for its fragrance resembling that of oranges and is used as a flavoring agent in the food industry. Additionally, D-limonene is utilized in chemical synthesis as a precursor to carvone and as a solvent in cleaning products based on renewable resources. The less common L-isomer, characterized by a piny, turpentine-like odor, is found in the edible parts of plants such as caraway, dill, and bergamot orange. The name "limonene" is derived from the Italian word "limone," meaning "lemon." Limonene is a chiral molecule, and biological sources typically produce only one enantiomer. The primary industrial source, citrus fruit, contains D-limonene ((+)-limonene), which is the (R)-enantiomer. Racemic limonene is known as dipentene. Commercially, D-Limonene is obtained from citrus fruits through methods like centrifugal separation or steam distillation.

First Aid

In case of exposure:

EYES: Check for contact lenses, flush eyes with water for 20-30 minutes, then seek medical help immediately.

SKIN: Wash affected skin with water and soap, remove contaminated clothing, and seek medical assistance promptly.

INHALATION: Leave contaminated area, breathe fresh air, call a physician, and provide respiratory protection. Seek medical help even if no symptoms occur.

INGESTION: Do not induce vomiting. If conscious, give water and seek medical advice. If unconscious, ensure open airway and seek immediate medical attention.

OTHER: Contact a physician for long-term health effects and medical monitoring recommendations based on exposure details (NTP, 1992).

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

136.23 g/mol

XLogP3-AA

3.4

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

0

Rotatable Bond Count

1

Exact Mass

136.125200510 g/mol

Monoisotopic Mass

136.125200510 g/mol

Topological Polar Surface Area

0Ų

Heavy Atom Count

10

Formal Charge

0

Complexity

163

Isotope Atom Count

0

Defined Atom Stereocenter Count

1

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

D-limonene is a clear colorless mobile liquid with a pleasant lemon-like odor. (NTP, 1992)

Boiling Point

177.6 °C

Melting Point

-74 °C

Density

0.8411 at 20 °C

Solubility 

Miscible with fixed oils; slightly soluble in glycerin; insoluble in propylene glycol

Vapor Pressure

1.98 [mmHg]

Source: PubChem

Source Species: Ocimum basilicum
Dioscorea dumetorum
Napoleonaea imperialis
Hirsute Palisota
Luffa cylindrica
Plumeria alba
Polyalthia suaveolens
Pyrenacantha staudtii
Tecoma stans
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