D(+)-Camphor
[CAS# 464-49-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: D(+)-Camphor
• Synonyms: (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• CAS Registry Number: 464-49-3
• EC Number: 207-355-2
• FEMA: 2230
• SMILES: C[C@@]12CC[C@@H](C1(C)C)CC2=O

Properties

• Solubility: 1600 mg/L (H2O, 25 ºC) (Expl.)
• Density: 1.0±0.1 g/mL, Calc.^*
• Melting point: 176-180 ºC (Expl.)
• Index of Refraction: 1.485, Calc.^*
• Boiling Point: 207.4 ºC (760 mmHg), Calc.^*, 204 ºC (Expl.)
• Flash Point: 64.4 ºC, Calc.^*, 64 ºC (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS08 Danger
• Hazard Statements: H228H302-H332-H371
• Precautionary Statements: P210-P240-P241-P260-P261-P264-P270-P271-P280-P301+P317-P304+P340-P308+P316-P317-P330-P370+P378-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable solids	Flam. Sol.	2	H228
Specific target organ toxicity - single exposure	STOT SE	2	H371
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	2	H330
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	3	H332
Acute toxicity	Acute Tox.	3	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Flammable liquids	Flam. Liq.	2	H226
Flammable liquids	Flam. Liq.	2	H225
Germ cell mutagenicity	Muta.	2	H341

Discovory and Applicatios

D(+)-Camphor is a natural compound derived from the wood of the camphor tree (Cinnamomum camphora), a large evergreen tree native to Asia. It is a bicyclic terpene ketone and is known for its distinct odor and various medicinal and industrial applications. The compound is used in a range of products, including medicinal formulations, cosmetics, and as a component in the fragrance industry.

The discovery of camphor dates back thousands of years, with its earliest recorded use in ancient China and India, where it was valued for its therapeutic properties. The isolation and identification of camphor as a specific compound were first achieved in the 19th century. D(+)-Camphor refers to the naturally occurring enantiomer of camphor, which is typically produced by distilling the wood of the camphor tree.

D(+)-Camphor has been widely used in the medical field for its various therapeutic properties. It is a well-known active ingredient in topical analgesic preparations and is commonly found in products designed to relieve minor aches and pains, such as muscle rubs, balms, and ointments. When applied to the skin, camphor produces a cooling sensation, which helps to alleviate discomfort by increasing blood flow to the affected area. This cooling effect also provides a soothing and anti-inflammatory action, making it a common remedy for conditions like sprains, strains, and joint pain.

In addition to its analgesic properties, D(+)-Camphor is also employed in the treatment of respiratory issues. It is used in many cough and cold medications, often in the form of inhalants or chest rubs. The compound helps to relieve congestion by stimulating the receptors in the respiratory tract, providing a cooling sensation that helps to clear the airways and improve breathing. It is a key ingredient in vapor rubs, which are applied to the chest to relieve symptoms of colds and bronchitis.

The compound also has a long history of use in the cosmetic and fragrance industries due to its strong scent and its ability to act as a stabilizing agent in various formulations. In perfumes, D(+)-Camphor is used for its fresh, sharp odor, which can enhance the overall fragrance profile of a product. It is particularly useful in the formulation of certain types of floral and herbal fragrances, where its scent can add complexity and depth.

D(+)-Camphor is also used in the manufacturing of plastics and as a plasticizer, where it helps to enhance the flexibility and durability of plastic materials. It is employed in the production of celluloid and other nitrocellulose-based plastics, which were historically important materials in the manufacture of items like buttons, combs, and film. Though its use in plastics has decreased in recent years, camphor is still used in some industrial applications.

In addition to its medicinal and industrial applications, D(+)-Camphor has been studied for its potential antimicrobial and antifungal properties. Some research suggests that it may possess mild antiseptic activity, making it useful in the formulation of disinfectants and products intended to cleanse the skin.

In conclusion, D(+)-Camphor is a versatile compound with a long history of use in medicine, cosmetics, fragrance, and industry. Its cooling and soothing properties make it valuable in the treatment of pain and respiratory conditions, while its distinctive scent and stabilizing effects are appreciated in perfumes and plastics. D(+)-Camphor continues to be an important compound with a broad range of applications in various sectors.

References

2024. Chemoselective Baeyer�Villiger Oxidation of R-(+)-Camphor with Caro's Acid. Russian Journal of Organic Chemistry, 60(9).
DOI: 10.1134/s1070428024090069

2024. Single Crystal Study, Spectroscopic Properties, Quantum DFT Calculations, Electrochemical and Thermal Behaviors of 1,3-Diketonato Ligand Derived from (+) (1R,4S)-3-Naphthoylcamphor. Russian Journal of Physical Chemistry A, 98(6).
DOI: 10.1134/s0036024424700158

2009. New enantiopure NHCs derived from camphor. Chemical Communications, (36).
DOI: 10.1039/b911476a