Camphor

Camphor^[1]^[2]
	; (+)- and (−)-camphor
Names
	IUPAC name 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
	Other names 2-Bornanone; Bornan-2-one; 2-Camphanone; Formosa
Identifiers
CAS Number	76-22-2 ; 464-49-3 (R) ; 464-48-2 (S) ;
3D model (JSmol)	Interactive image; Interactive image;
3DMet	B04902;
Beilstein Reference	1907611
ChEBI	CHEBI:36773 ;
ChEMBL	ChEMBL504760 ;
ChemSpider	2441 ; 7822160 (R) ; 9655 (S) ;
DrugBank	DB01744 ;
ECHA InfoCard	100.000.860
EC Number	200-945-0;
Gmelin Reference	83275
IUPHAR/BPS	2422;
KEGG	D00098 ;
MeSH	Camphor
PubChem CID	2537; 9543187 (R); 10050 (S);
RTECS number	EX1225000;
UNII	5TJD82A1ET ; N20HL7Q941 (R) ; 213N3S8275 (S) ;
UN number	2717
CompTox Dashboard (EPA)	DTXSID5030955 ;
	InChI InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3 Key: DSSYKIVIOFKYAU-UHFFFAOYSA-N ; InChI=1/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3 Key: DSSYKIVIOFKYAU-UHFFFAOYAK;
	SMILES CC1(C)C2CCC1(C)C(=O)C2; O=C1CC2CCC1(C)C2(C)C;
Properties
Chemical formula	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)
Solubility in water	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)
Chiral rotation ([α]D)	+44.1°
Magnetic susceptibility (χ)	−103×10−6 cm3/mol
Pharmacology
ATC code	C01EB02 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H228, H302, H332, H371
Precautionary statements	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)	2 2 0
Flash point	54 °C (129 °F; 327 K)
Autoignition; temperature	466 °C (871 °F; 739 K)
Explosive limits	0.6–3.5%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1310 mg/kg (oral, mouse)
LDLo (lowest published)	800 mg/kg (dog, oral); 2000 mg/kg (rabbit, oral)
LCLo (lowest published)	400 mg/m3 (mouse, 3 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 2 mg/m3
REL (Recommended)	TWA 2 mg/m3
IDLH (Immediate danger)	200 mg/m3
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). verify (what is ?) Infobox references

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.

^ The Merck Index, 7th edition, Merck & Co., Rahway, New Jersey, 1960
^ Handbook of Chemistry and Physics, CRC Press, Ann Arbor, Michigan, USA
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0096". National Institute for Occupational Safety and Health (NIOSH).
^ ^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.
^ 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.
^ "Rosemary". Drugs.com. Archived from the original on 14 September 2016. Retrieved 23 July 2016.
^ Lincoln, D.E.; Lawrence, B.M. (1984). "The volatile constituents of camphorweed, Heterotheca subaxillaris". Phytochemistry. 23 (4): 933–934. doi:10.1016/S0031-9422(00)85073-6.

[1] The Merck Index, 7th edition, Merck & Co., Rahway, New Jersey, 1960

[2] Handbook of Chemistry and Physics, CRC Press, Ann Arbor, Michigan, USA

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0096". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-4] "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. doi:10.1016/S0031-9422(00)85073-6.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Names
(+)- and (−)-camphor

IUPAC name 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
Other names 2-Bornanone; Bornan-2-one; 2-Camphanone; Formosa
Identifiers
CAS Number	76-22-2^Y 464-49-3 (R)^Y 464-48-2 (S)^Y
3D model (JSmol)	Interactive image Interactive image
3DMet	B04902
Beilstein Reference	1907611
ChEBI	CHEBI:36773^Y
ChEMBL	ChEMBL504760^N
ChemSpider	2441^Y 7822160 (R)^Y 9655 (S)^Y
DrugBank	DB01744^Y
ECHA InfoCard	100.000.860
EC Number	200-945-0
Gmelin Reference	83275
IUPHAR/BPS	2422
KEGG	D00098^Y
MeSH	Camphor
PubChem CID	2537 9543187 (R) 10050 (S)
RTECS number	EX1225000
UNII	5TJD82A1ET^Y N20HL7Q941 (R)^Y 213N3S8275 (S)^Y
UN number	2717
CompTox Dashboard (EPA)	DTXSID5030955
InChI InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3^Y Key: DSSYKIVIOFKYAU-UHFFFAOYSA-N^Y InChI=1/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3 Key: DSSYKIVIOFKYAU-UHFFFAOYAK
SMILES CC1(C)C2CCC1(C)C(=O)C2 O=C1CC2CCC1(C)C2(C)C
Properties
Chemical formula	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)
Solubility in water	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)
Chiral rotation ([α]_D)	+44.1°
Magnetic susceptibility (χ)	−103×10⁻⁶ cm³/mol
Pharmacology
ATC code	C01EB02 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H228, H302, H332, H371
Precautionary statements	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)	2 2 0
Flash point	54 °C (129 °F; 327 K)
Autoignition temperature	466 °C (871 °F; 739 K)
Explosive limits	0.6–3.5%^[3]
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	1310 mg/kg (oral, mouse)^[4]
LD_Lo (lowest published)	800 mg/kg (dog, oral) 2000 mg/kg (rabbit, oral)^[4]
LC_Lo (lowest published)	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 ^YN ?) Infobox references