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Trehalose

Catalog Number

ACM99207-4

CAS

99-20-7

Structure

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

Synonyms

D-Trehaloseanhydrous

Molecular Weight

342.3

Molecular Formula

C12H22O11

Canonical SMILES

C(C1C(C(C(C(O1)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O

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

InChI Key

HDTRYLNUVZCQOY-LIZSDCNHSA-N

Boiling Point

397.76 °C

Melting Point

203 °C

Flash Point

362.3 °C

Purity

98%

Density

1.5800 g/cm³

Solubility

Soluble in water

Appearance

White to off-white powder

Storage

Inert atmosphere, room temperature

Active Content

95%

Physical State

Powder

Typical Applications

Use as emulsion stabilizer, dispersing agent.

MSDS

Download MSDS

COA

Download COA

Spec Sheet

Download Spec Sheet

Case Study

Synthesis of 6-bromo-6-deoxy-2,3,4,2',3',4',6'-hepta-O-acetyl-trehalose (Tre(Ac)-Br) using Trehalose

Synthesis of 6-bromo-6-deoxy-2,3,4,2',3',4',6'-hepta-O-acetyl-trehalose (Tre(Ac)-Br) using Trehalose Li, Zongze, et al.Polymer 296 (2024): 126819.

Trehalose (4.10 g, 12.00 mmol) and PPh₃ (6.30 g, 24.00 mmol) were dissolved in DMF (40 mL). While stirring, NBS (4.28 g, 24.00 mmol) was added in small portions over 1 hour. The reaction mixture was stirred at room temperature for 48 hours. Then, the solvent was removed under reduced pressure, resulting in a yellow-brown solid. The product was washed with dichloromethane (DCM) and centrifuged to remove the supernatant. The product was then re-dissolved in pyridine (10 mL), and acetic anhydride (3.50 mL, 37.30 mmol) was added. The reaction mixture was stirred for an additional 12 hours, and the crude product was poured into water. It was then extracted three times with ethyl acetate (EtOAc), and the organic phases were combined. The solution was washed with NaHCO₃ and brine, dried over Na₂SO₄, and the solvent was removed under rotary evaporation. The crude product was purified by silica gel flash column chromatography (DCM/EtOAc = 4:1, Rf ~ 0.4) to yield a white solid (2.12 g, 25% yield).

Preparation of Trehalose Unsaturated Fatty Acid Diesters Using Trehalose

Preparation of Trehalose Unsaturated Fatty Acid Diesters Using Trehalose Ji, Suping, et al. Enzyme and Microbial Technology 136 (2020): 109516.

Trehalose diesters are gemini surfactants that may offer better surface activity than traditional surfactants. A one-step method for preparing trehalose unsaturated fatty acid diesters has been successfully developed.
Experimental Procedure: Weigh trehalose, unsaturated fatty acids, and immobilized lipase, and place them in a 25 mL screw-capped vial. Tighten the vial cap and add 10 mL of solvent. The vial is then immersed in a 50 °C water bath and continuously shaken at 150 rpm. At predetermined time intervals, 15 μL of the reaction mixture is withdrawn from the reactor for HPLC analysis.

Custom Q&A

What is the molecular formula of trehalose?

The molecular formula of trehalose is C12H22O11.

What is the molecular weight of trehalose?

The molecular weight of trehalose is 342.30 g/mol.

What is the IUPAC name of trehalose?

The IUPAC name of trehalose is (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.

Is trehalose used as a metabolite by Escherichia coli?

Yes, trehalose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).

What is the InChIKey of trehalose?

The InChIKey of trehalose is HDTRYLNUVZCQOY-LIZSDCNHSA-N.

How many hydrogen bond donor counts does trehalose have?

Trehalose has 8 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does trehalose have?

Trehalose has 11 hydrogen bond acceptor counts.

What is the XLogP3-AA value of trehalose?

The XLogP3-AA value of trehalose is -4.2.

What is the CAS number of trehalose?

The CAS number of trehalose is 99-20-7.

What is the exact mass of trehalose?

The exact mass of trehalose is 342.11621151 g/mol.

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