D-Glyceraldehyde

September 18, 2023
I’m a simple sugar that you can build on.
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Image of D-Glyceraldehyde 3D Image of D-Glyceraldehyde

D-Glyceraldehyde, a triose and the simplest aldose (aldehyde sugar), is an intermediate in fructose metabolism. It occurs in all living organisms, including humans. Its enantiomer, L-glyceraldehyde1, is related to the natural amino acids; but it does not occur in nature.

Racemic glyceraldehyde, along with dihydroxyacetone2, can be synthesized via the hydrogen peroxide oxidation of glycerol. Further oxidation of rac-glyceraldehyde produces rac-glyceric acid3 and eventually one- and two-carbon compounds.

D-Glyceraldehyde is an important starting material for the classic Kiliani–Fischer synthesis, which is used to build larger sugars from smaller ones. In this synthesis, D-glyceraldehyde reacts with cyanide ion to add a carbon atom at the aldehyde position. The nitrile group is then hydrolyzed and catalytically hydrogenated to produce the tetroses D-erythrose4 and D-threose5. Further iterations of the Kiliani–Fischer synthesis lead to higher aldoses.

D-Glyceraldehyde is also involved in shortening aldose chains, as exemplified by the Wohl degradation. It essentially accomplishes the reverse of the Kiliani–Fischer synthesis, so that D-erythrose and D-threose can be degraded to D-glyceraldehyde in a three-step process that, like Kiliani–Fischer, proceeds through a nitrile intermediate.

For additional information, see the ScienceDirect topic page on D-glyceraldehyde. And a question for readers: Crystalline D-glyceraldehyde has a relatively high melting point of 145 °C—so why is the article of commerce a viscous syrup?

1. CAS Reg. No. 497-09-6.
2. CAS Reg. No. 96-26-4.
3. CAS Reg. No. 473-81-4.
4. CAS Reg. No. 583-50-6.
5. CAS Reg. No. 95-43-2.


D-Glyceraldehyde hazard information

Hazard class* GHS code and hazard statement
Not a hazardous substance or mixture**  

*Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.
**Most safety data sheets give this description; but one lists five hazard classes.

Molecule of the Future

Milvexian1 is a developmental oral drug for preventing blood clots. It inhibits factor X1a (FX1a), an enzyme in the clot-forming coagulation cascade. Janssen Pharmaceuticals and Bristol-Myers Squibb (BMS) completed Phase 2 clinical trials on milvexian early this year.

In April, Simon Wagschal, Diego Broggini, and 35 colleagues at worldwide locations of Janssen and BMS reported a major advance toward the commercial synthesis of milvexian. They scaled up the reaction sequence for making the right-hand portion of the molecule (see image), which contains a 12-membered ring.

Molecule of  the Future: Milvexian is a developmental oral drug for preventing blood clots.

In June, Surasak Wichaiyo and co-workers at Mahidol University (Bangkok) reviewed the potential clinical benefits of small-molecule FXIa inhibitors for preventing arterial thrombosis. They focused on milvexian and another anticoagulant, asundexian2, along with mentions of other drug candidates in earlier stages of development. They concluded that small-molecule FXIa inhibitors have the advantages of rapid action, oral availability, and lower bleeding risks when compared with currently available anticoagulants.

1. CAS Reg. No. 1802425-99-5.
2. CAS Reg. No. 2064121-65-7.

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D-Glyceraldehyde fast facts

CAS Reg. No. 453-17-8
SciFinder nomenclature Propanal, 2,3-dihydroxy-, (2R)-
Empirical formula C3H6O3
Molar mass 90.08 g/mol
Appearance Colorless crystals or viscous liquid
Melting point 145 °C
Water solubility 29 g/L
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