Tryptophol

Structural formula
General
Surname	Tryptophol
other names	2- (1 H -indol-3-yl) ethanol; Indole-3-ethanol; Indole-3-ethyl alcohol; (Indol-3-yl) ethanol; 2-indolyl-3-ethanol;
Molecular formula	C 10 H 11 NO
External identifiers / databases
EC number	208-393-2
ECHA InfoCard	100.007.632
PubChem	10685
ChemSpider	10235
Wikidata	Q5479351
properties
Molar mass	161.20 g · mol
Physical state	Firmly
Melting point	59 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tryptophol is a chemical compound from the group of indole derivatives and alcohols .

Occurrence

Tryptophol occurs naturally in the needles and seeds of the Scots pine . In addition, tryptophol is produced as a secondary product during alcoholic fermentation and is contained in wine and beer. Tryptophol is also produced by the fungus Candida albicans or the sponge species Ircinia spiculosa .

Precursors for the synthesis of other compounds

Tryptophol was used as a starting material in the synthesis of dimethyltryptamine and indoramine .

Individual evidence

↑ ^a ^b ^c Data sheet 3- (2-Hydroxyethyl) indole, 98.0% from Sigma-Aldrich , accessed on April 14, 2017 ( PDF ).
↑ Göran Sandberg: Biosynthesis and metabolism of indole-3-ethanol and indole-3-acetic acid by Pinus sylvestris L. Needles . In: Planta . 161, No. 5, 1984, pp. 398-403. doi : 10.1007 / BF00394569 .
^ P Ribéreau-Gayon, JC Sapis: On the presence in wine of tyrosol, tryptophol, phenylethyl alcohol and gamma-butyrolactone, secondary products of alcoholic fermentation . In: Comptes rendus hebdomadaires des seances de l'Academie des sciences. Series D: Sciences naturelles . 261, No. 8, 1965, pp. 1915-6. PMID 4954284 . (Article in French)
^ C. Gil, C. Gómez-Cordovés: Tryptophol content of young wines made from Tempranillo, Garnacha, Viura and Airén grapes . In: Food Chemistry . 22, 1986, pp. 59-65. doi : 10.1016 / 0308-8146 (86) 90009-9 .
↑ BT Lingappa, M Prasad, Y Lingappa, DF Hunt, K Biemann: Phenethyl alcohol and tryptophol: Autoantibiotics produced by the fungus Candida albicans . In: Science . 163, No. 3863, 1969, pp. 192-4. doi : 10.1126 / science.163.3863.192 . PMID 5762768 .
↑ I Erdogan i, B Sener, T Higa: tryptophol, a plant auxin isolated from the marine sponge Ircinia spinulosa . In: Biochemical systematics and ecology . 28, No. 8, 2000, pp. 793-794. doi : 10.1016 / S0305-1978 (99) 00111-8 . PMID 10856636 .
↑ Dialkyltryptamines via tryptophol . Erowid.org. Retrieved August 18, 2013.

[Sigma-1] Data sheet 3- (2-Hydroxyethyl) indole, 98.0% from Sigma-Aldrich , accessed on April 14, 2017 ( PDF ).

[2] Göran Sandberg: Biosynthesis and metabolism of indole-3-ethanol and indole-3-acetic acid by Pinus sylvestris L. Needles . In: Planta . 161, No. 5, 1984, pp. 398-403. doi : 10.1007 / BF00394569 .

[3] P Ribéreau-Gayon, JC Sapis: On the presence in wine of tyrosol, tryptophol, phenylethyl alcohol and gamma-butyrolactone, secondary products of alcoholic fermentation . In: Comptes rendus hebdomadaires des seances de l'Academie des sciences. Series D: Sciences naturelles . 261, No. 8, 1965, pp. 1915-6. PMID 4954284 . (Article in French)

[4] C. Gil, C. Gómez-Cordovés: Tryptophol content of young wines made from Tempranillo, Garnacha, Viura and Airén grapes . In: Food Chemistry . 22, 1986, pp. 59-65. doi : 10.1016 / 0308-8146 (86) 90009-9 .

[5] BT Lingappa, M Prasad, Y Lingappa, DF Hunt, K Biemann: Phenethyl alcohol and tryptophol: Autoantibiotics produced by the fungus Candida albicans . In: Science . 163, No. 3863, 1969, pp. 192-4. doi : 10.1126 / science.163.3863.192 . PMID 5762768 .

[6] I Erdogan i, B Sener, T Higa: tryptophol, a plant auxin isolated from the marine sponge Ircinia spinulosa . In: Biochemical systematics and ecology . 28, No. 8, 2000, pp. 793-794. doi : 10.1016 / S0305-1978 (99) 00111-8 . PMID 10856636 .

[7] Dialkyltryptamines via tryptophol . Erowid.org. Retrieved August 18, 2013.