Camphor, (-)-

HCID 444294

Completing data — usually done within a minute

Basic information

CAS
464-48-2
Standard SMILES
CC1(C)[C@H]2CC[C@]1(C)C(=O)C2
InChIKey
DSSYKIVIOFKYAU-OIBJUYFYSA-N
Molecular formula
C10H16O
Average molar mass
152.23 g/mol
Monoisotopic mass
152.12011513

Overview

L-camphor appears as colorless or white crystals. Fragrant and penetrating odor. Slightly bitter and cooling taste. Odor index at 68 °F: 40. Flash point 149 °F. Burns with a bright, smoky flame. Sublimes appreciably at room temperature and pressure; 14% sublimes within 60 minutes at 176 °F and 12 mmHg. (NTP, 1992)

Names & identifiers

Preferred name
Camphor, (-)-
IUPAC
(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Names & synonyms

(-)-Camphorl-Camphor(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one(1S)-(-)-Camphor(S)-camphor(-)-Bornan-2-oneCamphor, (-)-DTXSID8022036(1S)-camphor()-bornan-2-one(1S,4S)-(-)-CAMPHORCAMPHOR, L-
Show more names
Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1S,4S)-CAMPHOR, (L)-CAMPHOR L-FORM [MI](S)-(-)-CAMPHORDTXCID502036213N3S8275Bicyclo(2.2.1)heptan-2-one, 1,7,7-trimethyl-, (1S,4S)-CHEBI:15397

Database identifiers

CAS
464-48-2
PubChem CID
444294
DTXSID
DTXSID8022036
ChEMBL
CHEMBL2252949
ChEBI
CHEBI:15397
UNII
213N3S8275
EC Number
207-354-7
Nikkaji
J67.498B

Properties

Computed structural propertiesFilling in

XLogP
2.2
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Plant Oils and Extracts
Density0.992 at 77 °F (NTP, 1992) - Less dense than water; will float
Solubility1 g/800 mL at 77 °F (NTP, 1992)
Flash Point150 °F (NTP, 1992)
Boiling Point399 °F at 760 mmHg (sublimes) (NTP, 1992)
Melting Point · 2 items

353.5 °F (NTP, 1992)

178-180

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H228 (35.5%): Flammable solid [Danger Flammable solids]

P203, P210, P240, P241, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 138 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1S)-

(1S)-(-)-Camphor: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1S)-: Environment tier I assessment
DOT LabelFlammable Solid
Fire HazardsThis chemical is flammable. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: Ingestion of this compound may cause nausea, vomiting, vertigo, mental confusion, delirium, convulsions, coma, respiratory failure or death. It may also cause a burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, severe irritation and possible destruction to the tissues of the mucous membranes, upper respiratory tract, eyes and skin. Other symptoms may include congestion and edematous changes in the gastrointestinal tract, kidneys and brain. Ingestion may result in burning in the mouth and throat, epigastric pain, thirst, feeling of tension, dizziness, irrational behavior, unconsciousness, rigidity, rapid pulse, slow respiration, twitching of the facial muscles and muscular spasms. Other symptoms may include flickering, darkening or veiling of vision, noises in the ears and weakness. Exposure to this compound may also result in a feeling of warmth, depression of the central nervous system, difficult breathing, a characteristic breath odor and anuria. Colic may also be a symptom of exposure. Other symptoms may include eye irritation, sore throat, excitement, fever, bluish lips, pale face, loss of sense of smell and agitation.

Hazards Summary · 1 item

May cause severe skin, eye, mucous membrane, and upper respiratory tract irritation; May cause CNS depression and other nervous system effects; Harmful by ingestion, inhalation, and skin absorption; [NTP] Causes convulsions in oral lethal-dose studies of rats; [RTECS] Camphor used topically during pregnancy in not likely to cause teratogenic effects; [TERIS] An irritant; Readily absorbed through skin; Targets the liver, kidney, and nerves; Ingestion may cause vertigo, confusion, clonic convulsions, coma, respiratory failure, and death; [Sigma-Aldrich MSDS] See Camphor, synthetic.

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 133 [Flammable Solids]:
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin

Chemistry & industry

Pharmacology

Protein BindingNo pharmacokinetic data available.
Pharmacodynamics · 1 item

Camphor exerts an analgesic action when applied topically by producing a warm sensation. It excites and desensitizes sensory nerves by activating heat-sensitive TRP vanilloid subtype 1 (TRPV1) and TRPV3 receptors. (S)-camphor is reported to exert a weaker action on TRPV1 channels, which is thought to be a result of tachyphylaxis, which is the reduction of the response to multiple stimulations.

Mechanism of Action · 1 item

TRPV3 cation channels are molecular sensors that play a role in nociception and thermosensation by inducing thermal sensation and heat-induced hyperalgesia. Camphor interacts with TRPV3 channels via pore-region cysteine residues, leading to channel activation and a rise in intracellular calcium levels. Camphor also activates TRPV1 and a TRPV1-like current in dorsal root ganglion (DRG) neurons but inhibits the ankyrin-repeat TRP 1 (TRPA1) channel expressed in most nociceptive DRG neurons, which is responsible for the detection of temperature. The precise role of TRPA1 current inhibition on the analgesic properties of camphor is unclear. Repeated stimulation by camphor leads to sensitization of the TRPV1 and TRPV3 channels, resulting in desensitization, or reduced channel response that likely leads to the analgesic effects of camphor. Camphor also activates cold-sensitive transient receptor potential melastatin 8 (TRPM8) and sensitizes cold-induced calcium transients, which explains the cooling effect of camphor following dermal application. Additionally, camphor was shown to inhibit the TRPM8 receptor response to menthol.

Biological Half-LifeFollowing oral ingestion of 200 mg camphor, the half life was 167 minutes.
Metabolism/Metabolites(S)-camphor undergoes rapid oxidation to 5-exo-hydroxyfenchone, which is predominantly mediated by human liver microsomal cytochrome (P450). CYP2A6 is the major enzyme involved in the hydroxylation of (-)-camphor by human liver microsomes.
Absorption, Distribution and Excretion · 4 items

Absorption of camphor in the mucous membranes and the gastrointestinal tract is rapid, and peak concentration following oral ingestion occurs within 5 to 90 minutes.

Camphor undergoes renal excretion.

Volume of distribution of camphor is 2 to 4 L/kg. Camphor and its metabolites are relatively fat-soluble thus may accumulate in adipose and other tissues. Camphor ingested by mothers was present in amnionic fluid, cord and fetal blood and fetal brain, liver and kidneys.

No pharmacokinetic data available.

Uses & manufacturing

Uses · 2 items

Naturally occurring form of camphor; Used in organic synthesis and as an odorant, flavoring agent, moth repellent, preservative, and plasticizer in cosmetics; Also used as a topical analgesic and antipruritic; [Merck Index] Used as a plasticizer for cellulose esters and ethers, to make plastics, cymene, and incense, in lacquers, varnishes, explosives, embalming fluids, pyrotechnics, and insect repellents; [NTP]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

General Manufacturing InformationBicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1S,4S)-: ACTIVE

Related reactions

3 records

Compound notes

Loading…