D-CAMPHOR

Description

(1R)-(+)-Camphor is a terpene that has been found in C. sativa, C. indica, and C. sativa/C. indica hybrid strains as well as the essential oils from a variety of herbs including rosemary, lavender, and sage and has diverse biological activities. It inhibits norepinephrine secretion and cytosolic calcium and sodium increases induced by the nicotinic acetylcholine receptor (nAChR) agonist 1,1-dimethyl-4-phenylpiperazinium iodide (DMPP) in chromaffin cells (IC₅₀s = 70, 88, and 19 μM, respectively). (1R)-(+)-Camphor (65-260 μM) induces proliferation of and increases expression of collagen IA, collagen IIIA, collagen IVA, and elastin in human primary dermal fibroblasts. In vivo, (1R)-(+)-camphor increases expression of collagen IA, collagen IIIA, collagen IVA, and elastin in skin in UV-exposed mice when administered at doses of 26 and 55 mM in drinking water post UV-exposure. It reduces cough frequency in citric acid-challenged guinea pigs. (1R)-(+)-Camphor is insecticidal, reducing digging activity and inducing mortality of fire ant workers. It has also been used as a building block in the synthesis of cannabinergic ligands.

Description

Camphor is a naturally occurring terpene found in trees in the laurel family (Lauraceae), notably camphor laurel, or Cinnamomum camphora, that is native to east and south Asia and now grows worldwide. It has been used in folk medicine for centuries.
Camphor can exist in two enantiomers: (+)- or (R)-camphor (shown), the predominant natural isomer, and (–)-or (S)-camphor1, which occurs in sand sage (Artemisia filifolia), a flowering plant native to the western United States. Synthetic camphor is usually a racemic mixture2 of the two enantiomers.
Camphor, with its familiar, penetrating odor, has a wide range of uses, including as a plasticizer for modified celluloses; in lacquers, varnishes, and plastics; as a moth repellent alternative to p-dichlorobenzene; and as a preservative in cosmetics and embalming fluids. In medicine, it is an ingredient in topical creams and ointments to treat itching, irritation, and joint pain; and it is used internally to prevent or relieve gas in the gastrointestinal tract.
1. CAS Reg. No. 464-48-2. 2. CAS Reg. No. 76-22-2.

Chemical properties

white crystals

Chemical properties

d-Camphor has a warm, minty, almost ethereal diffusive aroma. For other details of description, see Camphor Tree.

Occurrence

Frequently occurring in nature as the d- or l-form; the optically inactive form is seldom encountered. The d-form has been reported found in Cinnamomum camphora Ness. (Laurus camphora L.) from China, Japan and the East Indies; in Sassafras officinale, Lavandula spica and in other Labiatae. The l-form is reported found in the essential oils of Salvia grandiflora, Matricaria parthenium, Artemisia herba alba; the optically inactive form is found in Chrysanthemum japonicum sinense. Also reported found in orange peel oil, lemon peel oil, apricot, raspberry, anise, cinnamon root bark, ginger, pepper, coriander, calamus, sweet fennel and rosemary.

The Uses of D-CAMPHOR

D-Camphor may be used as reference material for the quantification of the analyte in Saraca asoca and coriander using chromatography techniques.

The Uses of D-CAMPHOR

(R)-(+)-Camphor is a terpenoid with a wide variety of use. (R)-(+)-Camphor has insecticidal activity and is also used as an antimicrobial agent. (R)-(+)-Camphor is used as a culinary flavouring agent in parts of asia.

The Uses of D-CAMPHOR

analgesic, antiinfective, antipruritic

The Uses of D-CAMPHOR

(1R)-(+)-Camphor is used as a chiral intermediate and auxiliary. It is also used as a skin antipruritic and as an anti-infective agent.

Background

Camphor is a bicyclic monoterpene ketone found widely in plants, especially Cinnamomum camphora. It is used topically as a skin antipruritic and as an anti-infective agent. When ingested, camphor has a rapid onset of toxic effects, and camphorated oil is the product most often responsible for its toxicity. The FDA ruled that camphorated oil could not be marketed in the United States and that no product could contain a concentration higher than 11%. It appears in the list of drug products withdrawn or removed from the market for safety or effectiveness. However, camphor can be found in several nonprescription medications at lower concentrations.

Definition

ChEBI: The (R)- enantiomer of camphor.

Aroma threshold values

Detection at 1 to 1.29 ppm

Taste threshold values

Taste characteristics at 20 ppm: medicinal, camphoraceous, mentholic and woody.

General Description

Colorless or white crystals. Sublimes. Flash point 149°F. Burns readily with a bright, smoky flame. Penetrating aromatic odor. Pungent, aromatic taste followed by a sensation of cold.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

D-CAMPHOR is incompatible with strong oxidizing agents, strong reducing agents and chlorinated solvents.

Fire Hazard

D-CAMPHOR is combustible.

Flammability and Explosibility

Flammable

Synthesis

Natural camphor is obtained by distillation from the plants of Cinnamomum or Laurus camphora from China and Japan, together with the corresponding essential oils; the raw camphor contains several impurities. It is separated from the water and the essential oil by pressure or by centrifugation and subsequently purified by sublimation or crystallization. Synthetic camphor is prepared from pinene isolated by fractional distillation of turpentine oil; pinene is reacted to bornyl chloride with gaseous HCl under pressure and then to camphene. The distilled and purified camphene is then oxidized to camphor with Na+ or K+ bichromate in the presence of H2SO4.

Metabolism

Purification Methods

Crystallise it from EtOH, 50% EtOH/water, MeOH, or pet ether or from glacial acetic acid by addition of water. It can be sublimed (50o/14mm) and also fractionally crystallised from its own melt. It is steam volatile. It should be stored in tight containers as it is appreciably volatile at room temperature. The solubility is 0.1% (H2O), 100% (EtOH), 173% (Et2O) and 300%