2D Structure

3D Structure

Limonene


Properties
PID PID00100
Mol. Weight 136.238 g/mol
LogP 3.22
Water solubility 0.65 to 2.1 mg/L
Hydrogen Bond Donor 0
Hydrogen Bond Acceptor 0
Rotatable Bonds 1
XLogP3-AA 3.4

Limonene

Identifiers
Formula C10H16
PubChem CID 22311
FEMA 2625
Flavor Profile Sweet, Citrus Taste, Characteristic Orange Taste, Characteristic Orange Odor, Pleasant Lemon-Like, Penetrating Odor,
Smiles CC1=CCC(CC1)C(=C)C
InChl Key XMGQYMWWDOXHJM-UHFFFAOYSA-N
InChl InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
CAS Registry Number 138-86-3, 65996-98-7, 7705-14-8, 5989-27-5, 8008-56-8, 8008-57-9, 8028-38-4, 0008008-57-9, 9003-73-0
IUPAC Systematic Name 1-methyl-4-prop-1-en-2-ylcyclohexene

Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets


Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)


Related Pungent TCM

English Name Pinyin Name (Chinese Name) Latin Name Properties in TCM merdians View Graph
NONENONENONENONENONEView Graph

Pharmacological action

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The D-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common L-isomer is found in mint oils and has a piny, turpentine-like odor.

Limonene is common as a dietary supplement and as a fragrance ingredient for cosmetics products. As the main fragrance of citrus peels, D-limonene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products. D-Limonene is also used as botanical insecticide. D-Limonene is used in the organic herbicide "Avenger". It is added to cleaning products, such as hand cleansers to give a lemon or orange fragrance (see orange oil) and for its ability to dissolve oils. In contrast, L-limonene has a piny, turpentine-like odor.

Limonene is used as a solvent for cleaning purposes, such as the removal of oil from machine parts, as it is produced from a renewable source (citrus oil, as a byproduct of orange juice manufacture). It is used as a paint stripper and is also useful as a fragrant alternative to turpentine. Limonene is also used as a solvent in some model airplane glues and as a constituent in some paints. Commercial air fresheners, with air propellants, containing limonene are used by philatelists to remove self-adhesive postage stamps from envelope paper.

Limonene is also used as a solvent for filament-fused 3D printing. Printers can print the plastic of choice for the model, but erect supports and binders from HIPS, a polystyrene plastic that is easily soluble in limonene. As it is combustible, limonene has also been considered as a biofuel.

In preparing tissues for histology or histopathology, D-limonene is often used as a less toxic substitute for xylene when clearing dehydrated specimens. Clearing agents are liquids miscible with alcohols (such as ethanol or isopropanol) and with melted paraffin wax, in which specimens are embedded to facilitate cutting of thin sections for microscopy. In traditional medicine, D-limonene is marketed to relieve gallstones, gastroesophageal reflux disease, and heartburn, although none of these supposed effects is confirmed by high-quality clinical research.



Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.

References

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