The lactol functional group, highlighted in blue, is present in many sugars such as ribose shown here.
In organic chemistry, a lactol is a functional group which is the cyclic equivalent of a hemiacetal (−CH(OH)O−) or a hemiketal (>C(OH)O−).
The compound is formed by the intramolecular, nucleophilic addition of a hydroxyl group (−OH) to the carbonyl group (C=O) of an aldehyde (−CH=O) or a ketone (>C=O).[1]
A lactol is often found as an equilibrium mixture with the corresponding hydroxyaldehyde. The equilibrium can favor either direction depending on ring size and other conformational effects.
The lactol functional group is prevalent in nature as component of aldose sugars.
In organic chemistry, a lactol is a functional group which is the cyclic equivalent of a hemiacetal (−CH(OH)O−) or a hemiketal (>C(OH)O−). The compound...
compound can exist in a monocyclic aldehyde form or in a bicyclic hemiacetal (lactol) form. It is unknown if glucuronolactone is safe for human consumption due...
the structure. Cyclic hemiacetals and hemiketals are sometimes called lactols. They often form readily, especially when they are 5- and 6-membered rings...
the lactol deoxydihydroartimisinin. These results show that the peroxy group assists the reduction of lactone with sodium borohydride to a lactol, but...
of strictosidine by strictosidine β-deglucosidase (SGD) produces a lactol. The lactol opens and produces an aldehyde, then condenses to form an iminium...
minor amounts of usnic acid and anhydrofusarubin lactol, and trace amounts of anhydrofusarubin lactol methyl ketal. The species epithet refers to the type...
converted to four possible sugars via Mukaiyama aldol addition followed by lactol formation. This requires appropriate diastereocontrol in the Mukaiyama aldol...
Lubiprostone, sold under the brand name Amitiza among others, is a medication used in the management of chronic idiopathic constipation, predominantly...
Nystatin, sold under the brand name Mycostatin among others, is an antifungal medication. It is used to treat Candida infections of the skin including...
Mitscher, L. A. (1994). "Alectosarmentin, a new antimicrobial dibenzofuranoid lactol from the lichen, Alectoria sarmentosa". Journal of Natural Products. 57...
of 1 met with undisclosed problems). The lactone is then reduced to the lactol 5b with diisobutylaluminum hydride and its liberated aldehyde reacts in...
skeleton with variable C-17 side chains containing actone, spirolactone, lactol, acetal, or furan moieties. They have been found to display cytotoxicity...
needed] Isaka I, Nakano K, Kashiwagi T, Koda A, Horiguchi H (January 1976). "Lactol esters of ampicillin". Chemical & Pharmaceutical Bulletin. 24 (1): 102–7...
spontaneous equilibrium between an open-chain hydroxy–ketone structure and a lactol form. Different experiments have shown the effects of the PR toxin on liver...
Naranol (W-5494A) is a drug having a tetracyclic[verification needed] structure. It was synthesized in the late 1960s, and was reported to have antidepressant...
DIMBOA (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one) is a naturally occurring hydroxamic acid, a benzoxazinoid. DIMBOA is a powerful antibiotic present...
intermediate 11 and 15 would be the next step. Using lithium borohydride, lactol arrangement of reagent 11 is reduced to create alcohol 16 which could be...
multifunctional scaffold for divergent synthesis. The reactants are the lactol derived from L-phenyl-lactic acid and acetone, l-phenylalanine methyl ester...
Botryodiplodin is an antibiotic mycotoxin produced by Penicillium. Cabedo, N; López-Gresa, MP; Primo, J; Ciavatta, ML; González-Mas, MC (2007). "Isolation...
Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation from soil from Nigeria was described in the 1950s, by R.L Harned (et...
oxidation of the 9β-pimara-7,15-diene compound followed by lactone and lactol formation yields momilactone B. Though the gene sequence of these oxidations...
Gummadiol is a lignan hemiacetal. It can be isolated from the heartwood of Gmelina arborea. Anjaneyulu, A.S.R.; Rao, A.Madhusudhana; Rao, V.Kameswara;...
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