|
|
| | D(+)-Trehalose dihydrate Basic information |
| | D(+)-Trehalose dihydrate Chemical Properties |
| Melting point | 97-99 °C(lit.) | | alpha | 179 º (c=2, H2O) | | Boiling point | 115.3 °C | | FEMA | 4600 | TREHALOSE, DIHYDRATE | | refractive index | 181 ° (C=7, H2O) | | storage temp. | room temp | | solubility | H2O: 50 mg/mL | | form | powder | | color | White to Off-White | | biological source | Saccharomyces cerevisiae | | Optical Rotation | [α]20/D +179±3°, c = 2% in H2O | | Water Solubility | 68.9 g/100 mL (20 ºC) | | Sensitive | Hygroscopic | | Merck | 14,9580 | | BRN | 5322018 | | InChI | 1S/C12H22O11.2H2O/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;2*1H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-;;/m1../s1 | | InChIKey | DPVHGFAJLZWDOC-NYAOJISMSA-N | | SMILES | [H]O[H].[H]O[H].OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O | | CAS DataBase Reference | 6138-23-4(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 38-36/37/38 | | Safety Statements | 37/39-26-24/25 | | WGK Germany | 2 | | RTECS | LZ5776547 | | F | 3-10 | | TSCA | Yes | | HS Code | 29400000 | | Storage Class | 11 - Combustible Solids |
| | D(+)-Trehalose dihydrate Usage And Synthesis |
| Description | Trehalose is a natural non-reducing disaccharide composed of two α-glucose units. It is found in all major groups of organisms except vertebrates, has biological functions as an osmolyte, storage reserve, and stress protectant, and has diverse commercial applications. Trehalose can also induce or enhance autophagy. | | Chemical Properties | D(+)-Trehalose dihydrate occurs as virtually odorless, white or almost white
crystals with a sweet taste (approximately 45% of the sweetness of
sucrose). | | Uses | Stabilizes cells during freezing, freeze-drying and air-drying. Sweetener and stabilizer in foods; cryoprotectant for freeze-dried foods. Additive in cosmetics and personal care products. | | Uses |
D(+)-Trehalose dihydrate is used in many processed foods as well as in biopharmaceutical monoclonal antibody formulations, it is also used as a protein stabilize.
| | Production Methods | Trehalose is prepared from liquefied starch by a multistep enzymatic
process. The commercial product is the dihydrate. | | Pharmaceutical Applications | D(+)-Trehalose dihydrate 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; for stabilization during the freeze–thaw and lyophilization
of liposomes; and for stabilization of blood cells,
cosmetics, and monoclonal antibodies. Trehalose may also be
used in formulations for topical application. | | Biochem/physiol Actions |
D(+)-Trehalose dihydrate is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond. It is thought to provide plants and animals with the ability to withstanding periods of dehydration.
| | Safety | 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.
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 | | Source | D(+)-Trehalose dihydrate is a natural alpha-linked disaccharide that is also referred to as mycose or tremalose. It is found naturally in plants and microorganisms such as grasshoppers, shrimp, butterflies and bees. | | storage | Trehalose is a relatively stable material. At 60°C 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 (≥90%).
Trehalose should be stored in a cool, dry place in a well-sealed
container. | | Purification Methods | α,α-D(+)-Trehalose crystallises (as the dihydrate) from aqueous EtOH. Dry it at 13o. For the anhydrous compound dissolve 10g in pyridine (200mL) and distil off this solvent at atmospheric pressure, and when the temperature rises to 115.3o all the H2O is removed and 73mL of distillate is collected. Most of the anhydrous material crystallises out at this stage. The crystals are collected (6.8g), washed with Et2O to give 6.1g of anhydrous product. Higher yields are obtained by slightly more prolonged distillation. [Birch J Chem Soc 3489 1965, X-ray cryst: Brown et al. Acta Cryst 28 3145 1972, Beilstein 17/8 V 3.] | | Incompatibilities |
D(+)-Trehalose dihydrate is incompatible with strong oxidizing agents, especially in the presence of heat.
| | Regulatory Status | GRAS listed. In the UK trehalose may be used in certain food
applications. Included in parenteral and nonparenteral investigational
formulations. | | References | [1] CARLOS M FIGUEROA J E L. A Tale of Two Sugars: Trehalose 6-Phosphate and Sucrose.[J]. Plant Physiology, 2016, 172 1: 7-27. DOI: 10.1104/pp.16.00417
[2] O J GODDIJN. Inhibition of trehalase activity enhances trehalose accumulation in transgenic plants.[J]. Plant Physiology, 1997, 113 1: 181-190. DOI: 10.1104/pp.113.1.181
[3] MAARTEN WALMAGH T D Renfei Zhao. Trehalose Analogues: Latest Insights in Properties and Biocatalytic Production.[J]. International Journal of Molecular Sciences, 2015, 16 6: 13729-13745. DOI: 10.3390/ijms160613729
[4] SAEID GHAVAMI . Autophagy and apoptosis dysfunction in neurodegenerative disorders[J]. Progress in Neurobiology, 2014, 112: Pages 24-49. DOI: 10.1016/j.pneurobio.2013.10.004 |
| | D(+)-Trehalose dihydrate Preparation Products And Raw materials |
|