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Xylitol is a chemical compound with the formula , or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular Stereoisomerism with that structural formula. It is a colorless or white solid. It is classified as a polyalcohol and a sugar alcohol, specifically an alditol. Of the common sugar alcohols, only sorbitol is more soluble in water.
The name derives from , xylon 'wood', with the suffix -itol used to denote it being a sugar alcohol.
Xylitol is used as a food additive and sugar substitute. Its E number is E967.
Replacing sugar with xylitol in food products may promote better dental health, but evidence is lacking on whether xylitol itself prevents dental cavities. In the United States, xylitol is used as a common sugar substitute, and is considered to be safe for humans.
Xylitol can be toxic to and ferrets.
Xylitol occurs naturally in small amounts in plums, strawberries, cauliflower, and pumpkin; humans and many other animals make trace amounts during metabolism of . Unlike most sugar alcohols, xylitol is achiral.
Most other of pentane-1,2,3,4,5-pentol are chiral, but xylitol has a plane of symmetry.Industrial production starts with lignocellulosic biomass from which xylan is extracted; raw biomass materials include , softwoods, and agricultural waste from processing maize, wheat, or rice. The mixture is hydrolyzed with acid to give xylose. The xylose is purified by chromatography. Purified xylose is catalytically hydrogenation into xylitol using a Raney nickel catalyst.
Xylitol can also be obtained by industrial fermentation, but this methodology is not as economical as the acid hydrolysis/chromatography route described above. Fermentation is effected by bacteria, fungi, or yeast, especially Candida tropicalis.
According to the US Department of Energy, xylitol production by fermentation from discarded biomass is one of the most valuable renewable chemicals for commerce, forecast to be a US $1.41 billion industry by 2025.
Xylitol has negligible effects on blood sugar because its assimilation and metabolism are independent of insulin. It is approved as a food additive and sugar substitute in the United States.
Xylitol is also found as an additive to saline solution for nasal irrigation and has been reported to be effective in improving symptoms of chronic sinusitis.
Xylitol can also be incorporated into fabrics to produce a cooling fabric. When moisture, such as sweat, comes into contact with the xylitol embedded in the fabric, it produces a cooling sensation.
Xylitol has about the same sweetness as sucrose, but is sweeter than similar compounds like sorbitol and mannitol.
Xylitol is stable enough to be used in baking, but because xylitol and other polyols are more heat-stable, they do not Caramelization as sugars do. When used in foods, they lower the freezing point of the mixture.
The real value can vary, depending on metabolic factors.
Primarily, the liver metabolizes absorbed xylitol. The main metabolic route in humans occurs in cytoplasm, via nonspecific NAD-dependent dehydrogenase (polyol dehydrogenase), which transforms xylitol to D-xylulose. Specific xylulokinase phosphorylates it to -xylulose-5-phosphate. This then goes to pentose phosphate pathway for further processing.
About 50% of eaten xylitol is absorbed via the intestines. Of the remaining 50% that is not absorbed by the intestines, in humans, 50–75% of the xylitol remaining in the gut is fermented by gut bacteria into short-chain organic acids and gases, which may produce flatulence. The remnant unabsorbed xylitol that escapes fermentation is excreted unchanged, mostly in feces; less than 2 g of xylitol out of every 100 g ingested is excreted via urine.
Xylitol ingestion also increases motilin secretion, which may be related to xylitol's ability to cause diarrhea.
The less-digestible but fermentable nature of xylitol also contributes to constipation relieving effects.
A 2016 review indicated that xylitol in chewing gum or a syrup may have a moderate effect in preventing AOM in healthy children.
It may be an alternative to conventional therapies (such as ) to lower risk of earache in healthy children – reducing risk of occurrence by 25%
– although there is no definitive proof that it could be used as a therapy for earache.
Xylitol products are used as sucrose substitutes for weight control,
as xylitol has 40% fewer calories than sucrose (2.4 kcal/g compared to 4.0 kcal/g for sucrose).
The glycemic index (GI) of xylitol is only 7% of the GI for glucose.
Xylitol has a lower laxation threshold than some sugar alcohols but is more easily tolerated than mannitol and sorbitol.
Increased xylitol consumption can increase oxalate, calcium, and phosphate excretion to urine (termed oxaluria, calciuria, and phosphaturia, respectively). These are known risk factors for kidney stone disease, but despite that, xylitol has not been linked to kidney disease in humans.
A 2018 study suggests that xylitol is safe for in doses of up to 1000 mg/kg; however, this study was performed on only 6 cats and should not be considered definitive.
The American Society for the Prevention of Cruelty to Animals has never issued any warning about xylitol and cats. A 2022 article by the organisation explicitly lists xylitol as non-toxic.
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