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(-)-Camphor

(-)-Camphor structure

(-)-Camphor 

structure
  • CAS No:

    464-48-2

  • Formula:

    C10H16O

  • Chemical Name:

    (-)-Camphor

  • Synonyms:

    Bicyclo[2.2.1]heptan-2-one,1,7,7-trimethyl-,(1S,4S)-;Camphor,(1S,4S)-(-)-;Bicyclo[2.2.1]heptan-2-one,1,7,7-trimethyl-,(1S)-;(1S,4S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one;l-Camphor;(-)-Camphor;(-)-Alcanfor;(1S)-(-)-Camphor;(1S)-Camphor;(1S,4S)-(-)-Camphor;NSC 26351;(S)-(-)-Camphor;(1S)-1,7,7-Trimethylbicyclo[2.2.1]-2-heptanone;(1S,4S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one

Description

white crystals


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 mm Hg. (NTP, 1992)


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 mm Hg. (NTP, 1992)|(S)-camphor is the S-enantiomer of camphor. It is an enantiomer of a (R)-camphor.|(S)-camphor, or L(-)-Camphor, is a stereoisomer of [DB01744], a bicyclic monoterpene known to potentiate both heat and cold sensations. (S)-camphor is not the naturally-occurring stereoisomer but displays similar TRPV channel affinity and current inhibition. [DB01744] is isolated from the wood of the camphor laurel tree, Cinnamomum camphora, and had a long history of medicinal use. It has been used as a nasal decongestant and cough suppressant, and has been topically applied due to its antipruritic, analgesic, and counterirritant properties. Camphor is a major active ingredient in over-the-counter balms and liniments supplied as topical analgesics by causing sensitization to heat and coolness to relieve minor muscle and joint pain.

(-)-Camphor Basic Attributes

152.23

152.23

207-354-7

213N3S8275

2717

DTXSID8022036

2914299000

Characteristics

17.1

2.2

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 mm Hg. (NTP, 1992)

1.0±0.1 g/cm3

175-178 °C

207.4°C at 760 mmHg

64.4±0.0 °C

1.485

Soluble in water. (0.34 g/L) at 20°C

4 mm Hg ( 70 °C)

5.24 (NTP, 1992) (Relative to Air)

Flammable. Slightly water soluble.

Ketones

L-CAMPHOR may be sensitive to heat and direct sunlight. Incompatible with strong oxidizing agents, strong reducing agents and chlorinated solvents. Also incompatible with potassium permanganate. Salts of any kind should not be added to it in water. Reacts violently with chromic anhydride (NTP, 1992).

871 °F (NTP, 1992)

Safety Information

4.1

2717

1

4.1

S16-S26-S37/39

EX1250000

F:Highlyflammable;Xi:Irritant;

Stable. Incompatible with strong reducing agents, strong oxidizing agents, chlorinated solvents. Protect from direct sunlight.

P210-P261-P305 + P351 + P338

H228-H315-H319-H335

This chemical is flammable. (NTP, 1992)

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 133 [Flammable Solids]: As an immediate precautionary measure, isolate spill or leak area for at least 25 meters (75 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 100 meters (330 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light, and store it under ambient temperatures. (NTP, 1992)

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. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)

Toxicity

Oral LD50 and intraperitoneal LD50 in mouse were 1310 mg/kg and 3000 mg/kg, respectively. Subcutaneous LD50 in rat was 70 mg/kg. The main target organs of camphor are the CNS and kidneys. Camphor is a CNS stimulant that may cause convulsions, depression, apnea, asystole, gastric irritation, colic, nausea, vomiting, diarrhea, anxiety, excitement, delirium, and severe post-convulsive coma. Camphor is also irritating to the eyes, skin and mucous membranes following dermal contact of high doses. Gastrointestinal irritation and CNS depression may occur at doses over 10 mg/kg while as little as 1 g has been fatal in infants, and death has been reported with doses of 50 mg/kg or more. There is no known antidote for camphor intoxication, thus gastrointestinal decontamination via activated charcoal is generally recommended for oral camphor overdose.

No pharmacokinetic data available.

Drug Information

Indicated for the temporary symptomatic relief of minor aches and pains of muscles and joints in topical analgesics.

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.

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.

(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.

Following oral ingestion of 200 mg camphor, the half life was 167 minutes.

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.

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. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of carbon monoxide and carbon dioxide. It is harmful if swallowed, inhaled or absorbed through the skin. It can be absorbed through mucous membranes. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)

(-)-Camphor Use and Manufacturing

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

Computed Properties

Molecular Weight:152.23
XLogP3:2.2
Hydrogen Bond Acceptor Count:1
Exact Mass:152.120115130
Monoisotopic Mass:152.120115130
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:217
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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