Réaction #1350569

ord-a9de046f2e654de5b5db01ec8e69c814

Équation de réaction

O=C(O)Cc1cc(O)ccc1O
Homogentisic acid
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2cc(O)ccc2O1
tocol
O=P(O)(O)O
H3PO4
Cc1c(O)cc2c(c1C)O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC2
γ-tocopherol
O=C(O)Cc1cc(O)ccc1O
Homogentisic acid
→
C/C(=C\Cc1cc(O)c(C)c(C)c1O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C
2,3-dimethyl-5-phytylquinol
C/C(=C\Cc1cc(O)cc(C)c1O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C
2-methyl-6-phytylquinol
C/C(=C\COP(=O)([O-])OP(=O)([O-])[O-])CCC[C@H](C)CCC[C@H](C)CCCC(C)C
Phytyl pyrophosphate

Réactifs

O=C(O)Cc1cc(O)ccc1O
Homogentisic acid
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2cc(O)ccc2O1
tocol
O=P(O)(O)O
H3PO4
Cc1c(O)cc2c(c1C)O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC2
γ-tocopherol
O=C(O)Cc1cc(O)ccc1O
Homogentisic acid

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

Homogentisic acid in 0.1% H3PO4 (specific radioactivity 40 Ci/mmol). Phytyl pyrophosphate was synthesized as described by Joo, et al. (1973) Can J. Biochem. 51: 1527. 2-methyl-6-phytylquinol and 2,3-dimethyl-5-phytylquinol were synthesized as described bySoll, et al. (1980) Phytochemistry 19: 215. Homogentisic acid, α, β, δ, and γ-tocopherol, and tocol, were purchased commercially.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06541259B1uspto-grants-2003_04