Chemical Properties
colourless liquid
Definition
ChEBI: An optically active form of limonene having (4R)-configuration.
General Description
Clear colorless mobile liquid with a pleasant lemon-like odor.
Reactivity Profile
D-LIMONENE(5989-27-5) is sensitive to exposure to light. Atmospheric oxidation can occur. This chemical is incompatible with strong oxidizing agents. D-LIMONENE(5989-27-5) reacts violently with (iodine pentafluoride + tetrafluoroethylene). With dry hydrogen chloride or hydrogen bromide, D-LIMONENE(5989-27-5) forms monohalides. With aqueous hydrogen chloride or hydrogen bromide, D-LIMONENE(5989-27-5) forms the dihalide.
Air & Water Reactions
Highly flammable. Insoluble in water.
Fire Hazard
This chemical is combustible.
Description
d-Limonene has a pleasant, lemon-like odors free from campho raceous and turpentine-like. d-Limonene may be obtained by
steam distillation of citrus peels and pulp resulting from the pro duction of juice and cold-pressed oils, or from deterpenation of
citrus oils; it is sometimes redistilled.
The most important and widespread terpene; it is known in the el and I- 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.
Occurrence
It has been reported found in more than 300 essential oils in amounts ranging from 90 to 95% (lemon, orange,
mandarin) to as low as 1% (palmarosa); the most widespread form is the d-limonene, followed by the racemic form and then l-limo nene. Also reported found in ginger, nutmeg, pepper, mace, hop oil, coriander seed, calamus, dill herb, caraway seed and rosemary.
Uses
Chiral building block. Biodegradable solvent. Limonene is used as a solvent for filament-fused 3D printing, in cosmetic products, as a fragrance and as a biofuel. It is useful to promote weight loss, prevent cancer, treat cancer and treat bronchitis. It also finds use in foods, beverages, chewing gum, as a flavoring agent and a shrinking agent to dissolve polystyrene. It acts as a chiral intermediate for natural product synthesis.
Preparation
d-Limonene may be obtained by steam distillation of citrus peels and pulp resulting from the production of juice and cold pressed oils, or from deterpenation of citrus oils; it is sometimes redistilled.
Aroma threshold values
Detection: 4 to 229 ppb
Taste threshold values
Taste characteristics at 30 ppm: sweet, orange, citrus and terpy.
Agricultural Uses
Insecticide, Animal and insect repellant, Slimicide: Used as an insecticide, insect repellent, and animal
repellent. Not listed for use in EU countries. Registered
for use in the U.S., Canada and other countries. There are
49 global suppliers.
Trade name
BUGAWAY®[C]; BUGCHASER®[C];
CARVENE®; DOO-NOT®; HOLIDAY FIRE ANT
KILLER®
Biochem/physiol Actions
Limonene is a cyclie terpene from Chinese medicinal herb essential oils used in the synthesis of carvone. Limonene may be used as a shrinking agent to dissolve polystyrene. Limonene may be used in various insecticidal and insect repellant applications.
Toxics Screening Level
The initial threshold screening level (ITSL) for d-limonene is 6,250 μg/m3 (annual averaging
time) based on the Michigan Department of Environmental Quality (MDEQ), Air Quality Division
(AQD) Rule 336.1229 (2) (b) and 336.1232 (1) (a).
References
[1] S. F. VAN VUUREN A. M V. Antimicrobial activity of limonene enantiomers and 1,8-cineole alone and in combination[J]. Flavour and Fragrance Journal, 2007, 22 6: 540-544. DOI:
10.1002/ffj.1843[2] SUN J. D-Limonene: safety and clinical applications.[J]. Alternative Medicine Review, 2007, 12 3: 259-264.
[3] MUNEEB U REHMAN. D-limonene suppresses doxorubicin-induced oxidative stress and inflammation via repression of COX-2, iNOS, and NFκB in kidneys of Wistar rats.[J]. Experimental Biology and Medicine, 2014, 239 4: 465-476. DOI:
10.1177/1535370213520112[4] Y. QIU. Delivery of RNAi Therapeutics to the Airways—From Bench to Bedside[J]. Molecules, 2016, 521 1. DOI:
10.3390/molecules21091249[5] XIAO-GUANG LU. Inhibition of growth and metastasis of human gastric cancer implanted in nude mice by d-limonene.[J]. World Journal of Gastroenterology, 2004, 10 14: 2140-2144. DOI:
10.3748/wjg.v10.i14.2140[6] L. KARR J C. Insecticidal properties of d-limonene[J]. Journal of Pesticide Science, 1988, 13 1: 287-290. DOI:
10.1584/jpestics.13.287
