THC Science

Isoborneol
Names
	IUPAC name (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;
PubChem CID	+: 6973640; -: 6321405;
UNII	+: 8GDX32M6KF; -: 20U67Z994U; rac: L88RA8N5EG;
UN number	1312
	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[edit]

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:

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

^ "(+)-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.