D-Camphor

Base Information

• Chemical Name: D-Camphor
• CAS No.: 464-49-3
• Deprecated CAS: 21368-68-3,48113-22-0,8013-55-6,8022-77-3,68546-28-1
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Hs Code.: 29142910
• European Community (EC) Number: 207-355-2,616-922-7
• NSC Number: 755918
• UN Number: 2717,1130
• UNII: N20HL7Q941,5TJD82A1ET
• DSSTox Substance ID: DTXSID4024721
• Nikkaji Number: J43.294F
• Wikidata: Q27089415
• NCI Thesaurus Code: C28136
• RXCUI: 1298738,1371994
• Metabolomics Workbench ID: 50062
• ChEMBL ID: CHEMBL504760
• Mol file: 464-49-3.mol

Synonyms:camphora

Chemical Property of D-Camphor

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 4 mm Hg ( 70 °C)
• Melting Point: 179-181 °C(lit.)
• Refractive Index: 44.5 ° (C=20, EtOH)
• Boiling Point: 207.4 °C at 760 mmHg
• Flash Point: 64.4 °C
• PSA: 17.07000
• Density: 0.982 g/cm³
• LogP: 2.40170
• Storage Temp.: 2-8°C
• Solubility.: Slightly soluble in water, very soluble in alcohol and in light petroleum, freely soluble in fatty oils, very slightly soluble in glycerol.
• Water Solubility.: Soluble in water (0.1 g/L at 20°C).
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 217
• Transport DOT Label: Flammable Solid

Purity/Quality:

99%, ^*data from raw suppliers

(R)-(+)-Camphor ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn, Xi
• Hazard Codes: F,Xn,Xi
• Statements: 11-22-36/37/38-20/21/22-36
• Safety Statements: 16-26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC1(C2CCC1(C(=O)C2)C)C
• Isomeric SMILES: C[C@@]12CC[C@@H](C1(C)C)CC2=O
• Recent EU Clinical Trials: Effects of
• 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.
• Uses: (1R)-(+)-Camphor is used as a chiral intermediate and auxiliary. It is also used as a skin antipruritic and as an anti-infective agent. D-Camphor may be used as reference material for the quantification of the analyte in Saraca asoca and coriander using chromatography techniques. (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. analgesic, antiinfective, antipruritic

Technology Process of D-Camphor

There total 169 articles about D-Camphor which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

d-borneol (464-43-7) → (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1)

Guidance literature:

With aluminum oxide; sodium bromite; In dichloromethane; for 24h; Ambient temperature;

Reference yield: 96.0%

isoborneol (124-76-5,464-43-7,464-45-9,507-70-0,6627-72-1,10334-13-1,10385-78-1,16725-71-6,24393-70-2) → (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1)

Guidance literature:

With 2-Picolinic acid; sodium nitrate; manganese (II) nitrate tetrahydrate; 9-azobicyclo[3.3.1]nonane N-oxyl; acetic acid; at 25 ℃; for 3h;

DOI:10.1002/cctc.201800438

Reference yield: 89.0%

(R,R)-camphor oxime (2792-42-9) → (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1)

Guidance literature:

With N,N'-dichlorobis(2,4,6-trichlorodiphenyl)urea; water; In acetonitrile; at 20 ℃; for 0.583333h;

DOI:10.3184/030823407X218093

upstream raw materials:

(+)-borneol

(1S,4S)-3-bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

3-diazocamphor

1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol

Downstream raw materials:

p-Anisylisoborneol

d-borneol

2-methyl-isoborneol

(+)-R-methylisoborneol

Refernces

Improved addition of phenyllithium to hindered ketones by the use of non-polar media

10.1016/S0040-4039(02)00597-X

The research focuses on the improved addition of phenyllithium (PhLi) to hindered ketones using non-polar media at room temperature. The study was conducted on six hindered ketones: (?)-fenchone, (?)-menthone, (+)-camphor, 3,3,5-trimethylcyclohexanone, 3,3,5,5-tetramethylcyclohexanone, and 2,4-dimethylpentan-3-one. The researchers aimed to enhance the low reactivity of these ketones towards PhLi, which traditionally yields modest results when performed in ethers like diethyl ether or THF. The experiments involved dissolving the ketones in a non-polar solvent, such as toluene or a toluene-diethyl ether mixture, and then slowly adding commercial PhLi via syringe. The mixtures were stirred at room temperature for 2 to 4 hours. The results showed significant improvements in yield compared to traditional methods, with the addition occurring in a stereospecific manner, favoring the less-hindered side. The configuration of the adducts was established using 13C NMR according to literature methods. This approach was found to be more efficient, cost-effective, and easier, offering a significant advantage for the synthesis of chiral inducers.