Back تريهالوز Arabic ترهالوز AZB Трэгалоза Byelorussian Trehalosa Catalan Trehalóza Czech Trehalose German Τρεχαλόζη Greek Trehalosa Spanish Trehalosa Basque ترهالوز Persian

Trehalose

Not to be confused with Trehalulose.
Trehalose
Names
IUPAC name
α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside
Systematic IUPAC name
(2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,4,5-triol
Other names
α,α‐Trehalose
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.490 Edit this at Wikidata
UNII
  • InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 checkY
    Key: HDTRYLNUVZCQOY-LIZSDCNHSA-N checkY
  • InChI=1/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
    Key: HDTRYLNUVZCQOY-LIZSDCNHBN
  • OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O1)O[C@@H]2[C@H](O)[C@@H](O)[C@H](O)[C@H](O2)CO
Properties
C12H22O11 (anhydride)
Molar mass 342.296 g/mol (anhydrous)
378.33 g/mol (dihydrate)
Appearance White orthorhombic crystals
Density 1.58 g/cm3 at 24 °C
Melting point 203 °C (397 °F; 476 K) (anhydrous)
97 °C (dihydrate)
68.9 g per 100 g at 20 °C[1]
Solubility Slightly soluble in ethanol, insoluble in diethyl ether and benzene[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trehalose (from Turkish tıgala – a sugar derived from insect cocoons + -ose)[3] is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it as a source of energy, and to survive freezing and lack of water.

Extracting trehalose was once a difficult and costly process, but around 2000, the Hayashibara company (Okayama, Japan) discovered an inexpensive extraction technology from starch.[4][5] Trehalose has high water retention capabilities, and is used in food, cosmetics and as a drug. A procedure developed in 2017 using trehalose allows sperm storage at room temperatures.[6]

  1. ^ Higashiyama T (2002). "Novel functions and applications of trehalose" (PDF). Pure Appl. Chem. 74 (7): 1263–1269. doi:10.1351/pac200274071263. S2CID 28311022.
  2. ^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–534. ISBN 978-0-8493-0594-8.
  3. ^ "Trehalose | Definition of Trehalose by Lexico". Archived from the original on February 26, 2022.
  4. ^ Cargill, Incorporated (30 May 2011). "Cargill, Hayashibara to Introduce Trehalose Sweetener to the Americas". PR Newswire. Retrieved 2011-07-31.
  5. ^ "JAPAN: Cargill, Hayashibara to Introduce Trehalose Sweetener to the Americas". just-food.com. 2000-05-31. Retrieved 2 February 2013.
  6. ^ Patrick, Jennifer L.; Elliott, Gloria D.; Comizzoli, Pierre (1 November 2017). "Structural integrity and developmental potential of spermatozoa following microwave-assisted drying in the domestic cat model". Theriogenology. 103: 36–43. doi:10.1016/j.theriogenology.2017.07.037. PMID 28772113.

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