Name: Trehalose
CAS No: (2R,3R,4S,5R,6R)-2-(Hydroxymethyl)-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxane-3,4,5-triol anhydrous [99-20-7], (2R,3R,4S,5R,6R)-2-(Hydroxymethyl)-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxane-3,4,5-triol dihydrate [6138-23-4]
None adopted.
Ascend; a-D-glucopyranosyl-a-D-glucopyranoside; (a-D-glucosido)- a-D-glucoside; mycose; natural trehalose; a,a-trehalose; Treha; trehalose dihydrate.
(2R,3R,4S,5R,6R)-2-(Hydroxymethyl)-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxane-3,4,5-triol anhydrous [99-20-7], (2R,3R,4S,5R,6R)-2-(Hydroxymethyl)-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxane-3,4,5-triol dihydrate [6138-23-4]
C12H22O11 342.31 (anhydrous) C12H22O112H2O 378.33 (dihydrate)
Trehalose is used for the lyoprotection of therapeutic proteins, particularly for parenteral administration. Other pharmaceutically relevant applications include use as an excipient for diagnostic assay tablets;(1) for stabilization during the freeze–thaw and lyophilization of liposomes;(2,3) and for stabilization of blood cells,(4) cosmetics,(5) and monoclonal antibodies.(6) Trehalose may also be used in formulations for topical application.(7)
Trehalose occurs as virtually odorless, white or almost white crystals with a sweet taste (approximately 45% of the sweetness of sucrose).(8)
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Acidity/alkalinity pH = 4.5–6.5 (30% w/v aqueous solution) Melting point 978C (for the dihydrate)(8) Moisture content 9.5% (for the dihydrate) Solubility Soluble in water; very slightly soluble in ethanol (95%); practically insoluble in ether. Specific rotation [a]D 20=þ179.78 (5% w/v aqueous solution)
Trehalose is a relatively stable material. At 608C for 5 hours it loses not more than 1.5% w/w of water (the dihydrate water of crystallization is retained). Open stored powder may liquefy at high relative humidity (590%). Trehalose should be stored in a cool, dry place in a well-sealed container.
Trehalose is incompatible with strong oxidizing agents, especially in the presence of heat.
Trehalose is prepared from liquefied starch by a multistep enzymatic process.(8) The commercial product is the dihydrate.
Trehalose is used in cosmetics, foods, and parenteral and nonparenteral pharmaceutical formulations. It is generally regarded as a relatively nontoxic and nonirritant material when used as an excipient. In the gut, trehalose is rapidly metabolized to glucose by the specific enzyme trehalase. A small minority of the population exhibits a primary (hereditary) or secondary (acquired) trehalase deficiency and thus may experience intestinal discomfort after ingestion of excessive amounts of trehalose owing to the osmotic activity of undigested trehalose in the gut. However, smaller amounts of trehalose are tolerated by such individuals without any symptoms.(8) Trehalose is used as a sweetener and is reported to have substantially less cariogenic potential than sucrose. LD50 (dog, IV): >1 g/kg LD50 (dog, oral): >5 g/kg LD50 (mouse, IV): >1 g/kg LD50 (mouse, oral): >5 g/kg LD50 (rat, IV): >1 g/kg LD50 (rat, oral): >5 g/kg
Observe normal precautions appropriate to the circumstances and quantity of material handled. Eye protection and gloves are recommended.
GRAS listed. In the UK trehalose may be used in certain food applications.(9) Included in parenteral and nonparenteral investigational formulations.
Isotrehalose; neotrehalose. Isotrehalose CAS number [499-23-0] Synonyms b,b-Trehalose. Neotrehalose CAS number [585-91-1] Synonyms a,b-Trehalose.
a,a-Trehalose is the only naturally occurring isomer of trehalose and occurs as the dihydrate. However, a,b-trehalose (neotrehalose) and b,b-trehalose (isotrehalose) have been synthesized and are also available commercially. Trehalose is a nonreducing sugar and therefore does not react with amino acids or proteins as a part of Maillard browning. It is relatively stable under low-pH conditions compared to other disaccharides. It should be noted that although trehalose dihydrate is quoted to have a melting point of 978C, the true nature of this melting process has been the subject of debate in the literature,(10–12) including the transformation of the dihydrate into the anhydrous form. Anhydrous crystalline trehalose has been reported to melt at 2038C,(13) although higher values (2158C) have also been quoted in the literature.(14) The glass transition temperature of trehalose is reported to be approximately 1208C (anhydrous amorphous phase).(15) The EINECS number for trehalose is 202-739-6. The PubChem Compound ID (CID) for trehalose is 7427.