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This makes the hydroxymethyl group an alcohol. It has the identical chemical formula with the methoxy group (−O−CH 3) that differs only in the attachment site and orientation to the rest of the molecule. However, their chemical properties are different. [1] [2] Hydroxymethyl is the side chain of encoded amino acid serine. [3]
9-Anthracenemethanol is the derivative of anthracene with a hydroxymethyl group (CH 2 OH) attached to the 9-position. It is a colorless solid that is soluble in ordinary organic solvents. The compound can be prepared by hydrogenation of 9-anthracenecarboxaldehyde. It is a versatile precursor to supramolecular assemblies.
A common method for hydroxymethylation involves the reaction of formaldehyde with active C-H and N-H bonds: R 3 C-H + CH 2 O → R 3 C-CH 2 OH R 2 N-H + CH 2 O → R 2 N-CH 2 OH. A typical active C-H bond is provided by a terminal acetylene [1] or the alpha protons of an aldehyde. [2]
The initial reaction in all cases involves the formation of a hydroxymethyl phenol: HOC 6 H 5 + CH 2 O → HOC 6 H 4 CH 2 OH. The hydroxymethyl group is capable of reacting with either another free ortho or para site, or with another hydroxymethyl group. The first reaction gives a methylene bridge, and the second forms an ether bridge:
Cyclohexylmethanol is an organic compound with the formula C 6 H 11 −CH 2 −OH. It is a cyclohexane ring functionalized with an alcohol, specifically a hydroxymethyl group. The compound is a colorless liquid, although commercial samples can appear yellow.
Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents. [4]
5-Hydroxymethylcytosine was observed by Skirmantas Kriaucionis, an associate at the Heintz lab, who was looking for levels of 5-methylcytosine in two different neuron types. He discovered a significant amount of an unknown substance instead, and after conducting several tests, identified it as being 5-hydroxymethylcytosine.
Salicyl alcohol (saligenin) is an organic compound with the formula C 6 HOH(CH 2 OH. It is a white solid that is used as a precursor in organic synthesis . [ 3 ]