Isolation of new constituents with a formyl group from the heartwood of Santalum album L.

Abstract

Sandalwood (Santalum album L.) is a traditional incense, and its essential oil is used in fragrances. The hexane extract from Indian sandalwood chips had a sandalwood odour similar to sandalwood chips, but it clearly differed from that of commercial essential oil. By fractional distillation of the extract under reduced pressure, a fraction was obtained that had a sandalwood-like odour and contained several unknown formyl compounds as the main constituents. Santalyl formates were isolated as new components from this fraction by chromatography and characterized by 1 H-and 13 C-NMR spectroscopy. These constituents were less abundant in the commercial essential oil than in the hexane extract. Santalyl formates were synthesized from the corresponding alcohols.

Phytochemistry of the heartwood from fragrant Santalum species: a review

“…[18] One can speculate whether the thermal process during the hydrodistillation and/or the GC experiment was not able to induce (at least partly) this isomerization, which could then explain why the co-occurrence of (E) and (Z) was described in many studies. [9,29,30] However, the four isomers 140-142 and 144 were observed (by 1 H-NMR) in a solvent extract distilled and fractionated by PTLC (on silica gel), [31] while the (E) isomers of a-and b-santalals were identified ( 1 H-NMR) in a cold methanolic extract fractionated by CC on silica gel and HPLC. [28] This last experiment may support the natural occurrence of the (E) isomers, as the (Z)-santalals are usually sufficiently stable to be submitted to chromatographic separations on silica gel without the likelyhood of isomerization.…”

“…A, [18] S [29] *, AC, [9] I [33] A, [31] S [29] *, AC, [9] I [33] A, [18] S [29] 149 (E)-Nuciferal A, [11] I [33] 150 (E,E)- A, [10] AC [9] 152 Cyclosantalal h 168099-27-2…”

Characteristic Changes in the Aroma Profile of Patchouli Depending on Manufacturing Process

“…We encountered the same problem during investigating the odor of sandalwood 5 , and solved it by using bulb-to-bulb distillation. We applied the same approach to investigating the aroma profile of patchouli.…”

Biological Activities of East Indian Sandalwood Tree, Santalum album

“…The phytochemistry of heartwood constituents, more than of them, reported from several sandalwood species have been reviewed extensively (Baldovini et al, 2011). Newer sesquiterpenoid constituents i.e., santalyl formates (Hasegawa et al, 2011) are being discovered every year. Very recently, sandalwood essential oil was shown to be among one Joe, 2012) have provided essential resources for advanced and rapid research in sandalwood oil and wood.…”