Isoborneol

Isoborneol
Names
	IUPAC names +: (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol; -: (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol
Identifiers
CAS Number	+: 16725-71-6 d; -: 10334-13-1; rac: 124-76-5;
3D model (JSmol)	+: Interactive image; -: Interactive image; rac: Interactive image;
ChEBI	+: CHEBI:191949;
ChEMBL	+: ChEMBL4294644; -: ChEMBL3560760;
ChemSpider	+: 16739225; -: 4882019;
ECHA InfoCard	100.004.285
PubChem CID	+: 6973640; -: 6321405;
UNII	+: 8GDX32M6KF; -: 20U67Z994U; rac: L88RA8N5EG;
UN number	1312
CompTox Dashboard (EPA)	+: DTXSID2042060 ;
	InChI +: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1 Key: DTGKSKDOIYIVQL-OYNCUSHFSA-N; -: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1 Key: DTGKSKDOIYIVQL-MRTMQBJTSA-N;
	SMILES +: C[C@]12CC[C@H](C1(C)C)C[C@@H]2O; -: C[C@@]12CC[C@@H](C1(C)C)C[C@H]2O; rac: CC1(C2CCC1(C(C2)O)C)C;
Properties
Chemical formula	C10H18O
Molar mass	154.253 g·mol−1
Appearance	white or colorless solid
Melting point	212–214 °C (414–417 °F; 485–487 K) + or -; 210–215 °C for rac
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H228
Precautionary statements	P210, P240, P241, P280, P370+P378
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isoborneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an exo position. The endo diastereomer is called borneol. Being chiral, isoborneol exists as enantiomers.

Preparation

Isoborneol is synthesized commercially by hydrolysis of isobornyl acetate. The latter is obtained from treatment of camphene with acetic acid in the presence of a strong acid catalyst.^[2]

It can also be produced by reduction of camphor:

Isoborneol derivatives as chiral ligands

Derivatives of isoborneol are used as ligands in asymmetric synthesis.^[3]

(2S)-(−)-3-exo-(morpholino)isoborneol or MIB^[4] with a morpholine substituent in the α-hydroxyl position.
(2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB^[5] with a dimethylamino substituent in the α-hydroxyl position

References

^ "(+)-Isoborneol". pubchem.ncbi.nlm.nih.gov. Retrieved 1 December 2022.
^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
^ Yus, Miguel; Ramón, Diego (2007). "Chiral Ligands with an Isoborneol-10-sulfonamide Structure: A Ten-Year Odyssey". Synlett. 2007 (15): 2309–2320. doi:10.1055/s-2007-985602.
^ Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005). "(2S)-(−)-3-exo-(Morpholino)isoborneol". Organic Syntheses. 82: 87. doi:10.15227/orgsyn.082.0087.
^ White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(Dimethylamino)isoborneol". Organic Syntheses. 79: 130. doi:10.15227/orgsyn.079.0130.

[1] "(+)-Isoborneol". pubchem.ncbi.nlm.nih.gov. Retrieved 1 December 2022.

[2] Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.

[3] Yus, Miguel; Ramón, Diego (2007). "Chiral Ligands with an Isoborneol-10-sulfonamide Structure: A Ten-Year Odyssey". Synlett. 2007 (15): 2309–2320. doi:10.1055/s-2007-985602.

[4] Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005). "(2S)-(−)-3-exo-(Morpholino)isoborneol". Organic Syntheses. 82: 87. doi:10.15227/orgsyn.082.0087.

[5] White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(Dimethylamino)isoborneol". Organic Syntheses. 79: 130. doi:10.15227/orgsyn.079.0130.

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