Borneol
























































































































Borneol





Borneol


Borneol-3D-balls.png


Names

IUPAC name

endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol

Identifiers

CAS Number



  • 507-70-0 ☑Y


3D model (JSmol)


  • Interactive image


ChEBI


  • CHEBI:15393 ☑Y


ChEMBL


  • ChEMBL486208 ☑Y


ChemSpider


  • 5026296 ☑Y


ECHA InfoCard

100.006.685

IUPHAR/BPS


  • 6413


KEGG


  • C01411 ☑Y



PubChem CID


  • 6552009


UNII


  • M89NIB437X ☑Y





Properties

Chemical formula


C10H18O

Molar mass

7002154253000000000♠154.253 g·mol−1
Appearance
colorless to white lumps

Odor
pungent, camphor-like

Density
1.011 g/cm3 (20 °C)[1]

Melting point
208 °C (406 °F; 481 K)

Boiling point
213 °C (415 °F; 486 K)

Solubility in water

slightly soluble (D-form)

Solubility
soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin


Magnetic susceptibility (χ)


3003874000000000000♠−1.26×10−4 cm3/mol
Hazards

Safety data sheet

External MSDS

NFPA 704



Flammability code 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 fuel
Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform
Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen
Special hazards (white): no code
NFPA 704 four-colored diamond


2


2


0



Flash point
65 °C (149 °F; 338 K)
Related compounds

Related compounds


Bornane (hydrocarbon)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


☑Y verify (what is ☑Y☒N ?)

Infobox references



Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. There are two different enantiomers of borneol. Both d-(+)-borneol and l-(–)-borneol are found in nature.




Contents






  • 1 Reactions


  • 2 Natural occurrences


  • 3 Uses


    • 3.1 Use in organic chemistry




  • 4 Toxicology


  • 5 Derivatives


  • 6 Notes and references


  • 7 External links





Reactions


Borneol is easily oxidized to the ketone (camphor). One historical name for borneol is Borneo camphor which explains the name. (The compound was named in 1842 by the French chemist Charles Frédéric Gerhardt.[2]) Borneol can be synthesized by reduction of camphor by the Meerwein–Ponndorf–Verley reduction (a reversible process). Reduction of camphor with sodium borohydride (fast and irreversible) gives instead the isomer isoborneol as the kinetically controlled reaction product.





Synthesis of the borneol isomer isoborneol via reduction of camphor.





Natural occurrences


Borneol can be found in several species of Heterotheca,[3]Artemisia, Callicarpa[4], Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga.[5]


It is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's plant food.[6]



Uses


Whereas d-borneol was the enantiomer that used to be the most readily available commercially, the more commercially available enantiomer now is l-borneol, which also occurs in nature.


Borneol is used in traditional Chinese medicine. An early description is found in the Bencao Gangmu.


Borneol is a component of many essential oils[7] and it is a natural insect repellent.[8]



Use in organic chemistry


Derivatives of isoborneol are used as chiral ligands in asymmetric synthesis:



  • (2S)-(−)-3-exo-(morpholino)isoborneol or MIB[9] with a morpholine substituent in the α-hydroxyl position

  • (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB[10] with a dimethylamino substituent in the α-hydroxyl position



Toxicology


Borneol is an eye, skin, and respiratory irritant; it is harmful if swallowed.[11]



Derivatives


The bornyl group is a univalent radical C10H17 derived from borneol by removal of hydroxyl and is also known as 2-bornyl.[12] Isobornyl is the univalent radical C10H17 that is derived from isoborneol.[13]


Bornyl acetate is the acetate ester of borneol.



Notes and references





  1. ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. p. 3.56. ISBN 0-8493-0486-5..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  2. ^ C. Gerhardt (1842) "Sur la transformation de l'essence de valériane en camphre de Bornéo et en camphre des laurinées" (On the transformation of the essence of valerian into Borneo camphor and into laurel camphor), Comptes rendus, 14 : 832-835. From p. 834: "Je donne, par cette raison, à l'hydrogène carboné de l'essence de valériane, le nom de bornéène, et, au camphre lui-même, celui de bornéol." (I give, for this reason [namely, that the compound that Gerhardt had obtained from valerian oil was identical to that obtained by Pelouze from camphor from Borneo], to the hydrocarbon from valerian essence, the name bornéène, and, to camphor itself, that of borneol.)


  3. ^ Lincoln, D.E., B.M. Lawrence. 1984. "The volatile constituents of camphorweed, Heterotheca subaxillaris".
    Phytochemistry 23(4): 933-934



  4. ^ "Species Information". sun.ars-grin.gov. Retrieved 2008-03-02.


  5. ^ Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Composition of the essential oil of rhizomes of Kaempferia Galanga L.". Flavour and Fragrance Journal. 7 (5): 263–266. doi:10.1002/ffj.2730070506.


  6. ^ The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)


  7. ^ Plants containing borneol Archived 2015-09-23 at the Wayback Machine (Dr. Duke's Phytochemical and Ethnobotanical Databases)]


  8. ^ "Chemical Information". sun.ars-grin.gov. Archived from the original on 2004-11-07. Retrieved 2008-03-02.


  9. ^ Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005). "(2S)-(–)-3-exo-(MORPHOLINO)ISOBORNEOL [(–)-MIB]" (PDF). Organic Syntheses. 82: 87.; Collective Volume, 11, p. 702


  10. ^ White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]" (PDF). Organic Syntheses. 79: 130.; Collective Volume, 10, p. 305
    [permanent dead link]



  11. ^ Material Safety Data Sheet, Fisher Scientific


  12. ^ "Definition of BORNYL". www.merriam-webster.com.


  13. ^ "Definition of ISOBORNYL". www.merriam-webster.com.




External links



  • NIST datasheet including full spectroscopic data

  • Borneol in Chinese medicine








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