Trehalose

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
CAS Number	99-20-7 (anhydrous) ; 6138-23-4 (dihydrate) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16551 ;
ChEMBL	ChEMBL1236395 ;
ChemSpider	7149 ;
ECHA InfoCard	100.002.490
PubChem CID	7427;
UNII	B8WCK70T7I ;
CompTox Dashboard (EPA)	DTXSID3048102 ;
	InChI 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 Key: HDTRYLNUVZCQOY-LIZSDCNHSA-N ; 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;
	SMILES 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
Chemical formula	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)
Solubility in water	68.9 g per 100 g at 20 °C
Solubility	Slightly soluble in ethanol, insoluble in diethyl ether and benzene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

^ Higashiyama T (2002). "Novel functions and applications of trehalose" (PDF). Pure Appl. Chem. 74 (7): 1263–1269. doi:10.1351/pac200274071263. S2CID 28311022.
^ 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.
^ "Trehalose | Definition of Trehalose by Lexico". Archived from the original on February 26, 2022.
^ Cargill, Incorporated (30 May 2011). "Cargill, Hayashibara to Introduce Trehalose Sweetener to the Americas". PR Newswire. Retrieved 2011-07-31.
^ "JAPAN: Cargill, Hayashibara to Introduce Trehalose Sweetener to the Americas". just-food.com. 2000-05-31. Retrieved 2 February 2013.
^ 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.

[1] Higashiyama T (2002). "Novel functions and applications of trehalose" (PDF). Pure Appl. Chem. 74 (7): 1263–1269. doi:10.1351/pac200274071263. S2CID 28311022.

[hand-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.

[jfood-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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