Camphor

Not to be confused with samphor.
For other uses, see Camphor (disambiguation).
Camphor[1][2]
Structural formula of (R) and (S)-camphor
(+)- and (−)-camphor
Ball and stick model of camphor (both enantiomers).
Names
IUPAC name
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
Other names
2-Bornanone; Bornan-2-one; 2-Camphanone; Formosa
Identifiers
3D model (JSmol)
3DMet
1907611
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.860 Edit this at Wikidata
EC Number
  • 200-945-0
83275
KEGG
MeSH Camphor
RTECS number
  • EX1225000
UNII
UN number 2717
  • InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3 checkY
    Key: DSSYKIVIOFKYAU-UHFFFAOYSA-N checkY
  • InChI=1/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3
    Key: DSSYKIVIOFKYAU-UHFFFAOYAK
  • CC1(C)C2CCC1(C)C(=O)C2
  • O=C1CC2CCC1(C)C2(C)C
Properties
C10H16O
Molar mass 152.237 g·mol−1
Appearance White, translucent crystals
Odor Fragrant and penetrating
Density 0.992 g·cm−3
Melting point 175–177 °C (347–351 °F; 448–450 K)
Boiling point 209 °C (408 °F; 482 K)
1.2 g·dm−3
Solubility in acetone ~2500 g·dm−3
Solubility in acetic acid ~2000 g·dm−3
Solubility in diethyl ether ~2000 g·dm−3
Solubility in chloroform ~1000 g·dm−3
Solubility in ethanol ~1000 g·dm−3
log P 2.089
Vapor pressure 4 mmHg (at 70 °C)
+44.1°
−103×10−6 cm3/mol
Pharmacology
C01EB02 (WHO)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Warning
H228, H302, H332, H371
P210, P240, P241, P260, P261, P264, P270, P271, P280, P301+P312, P304+P312, P304+P340, P309+P311, P312, P330, P370+P378, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 54 °C (129 °F; 327 K)
466 °C (871 °F; 739 K)
Explosive limits 0.6–3.5%[3]
Lethal dose or concentration (LD, LC):
1310 mg/kg (oral, mouse)[4]
800 mg/kg (dog, oral)
2000 mg/kg (rabbit, oral)[4]
400 mg/m3 (mouse, 3 hr)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 2 mg/m3[3]
REL (Recommended)
 TWA 2 mg/m3[3]
IDLH (Immediate danger)
 200 mg/m3[3]
Related compounds
Related Ketones
 Fenchone, Thujone
Related compounds
 Camphene, Pinene, Borneol, Isoborneol, Camphorsulfonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Camphor (/ˈkæmfər/) is a waxy, colorless solid with a strong aroma.[5] It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (Cinnamomum camphora), a large evergreen tree found in East Asia; and in the kapur tree (Dryobalanops sp.), a tall timber tree from South East Asia. It also occurs in some other related trees in the laurel family, notably Ocotea usambarensis. Rosemary leaves (Rosmarinus officinalis) contain 0.05 to 0.5% camphor,[6] while camphorweed (Heterotheca) contains some 5%.[7] A major source of camphor in Asia is camphor basil (the parent of African blue basil). Camphor can also be synthetically produced from oil of turpentine.

The compound is chiral, existing in two possible enantiomers as shown in the structural diagrams. The structure on the left is the naturally occurring (+)-camphor ((1R,4R)-bornan-2-one), while its mirror image shown on the right is the (−)-camphor ((1S,4S)-bornan-2-one). Camphor has few uses but is of historic significance as a compound that is readily purified from natural sources.

  1. ^ The Merck Index, 7th edition, Merck & Co., Rahway, New Jersey, 1960
  2. ^ Handbook of Chemistry and Physics, CRC Press, Ann Arbor, Michigan, USA
  3. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0096". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ a b c "Camphor (synthetic)". National Institute for Occupational Safety and Health (NIOSH). 4 December 2014. Archived from the original on 13 March 2015. Retrieved 19 February 2015.
  5. ^ Mann JC, Hobbs JB, Banthorpe DV, Harborne JB (1994). Natural products: their chemistry and biological significance. Harlow, Essex, England: Longman Scientific & Technical. pp. 309–11. ISBN 978-0-582-06009-8.
  6. ^ "Rosemary". Drugs.com. Archived from the original on 14 September 2016. Retrieved 23 July 2016.
  7. ^ Lincoln, D.E.; Lawrence, B.M. (1984). "The volatile constituents of camphorweed, Heterotheca subaxillaris". Phytochemistry. 23 (4): 933–934. Bibcode:1984PChem..23..933L. doi:10.1016/S0031-9422(00)85073-6.