What molecule am I?
D-Glyceric acid is a sugar acid and an oxidation product of glycerol. It is a natural product, occurring as a glycerol metabolite in humans and in species ranging from the fruit fly (Drosophila melanogaster) to the common aspen (Populus tremula). Its enantiomer L-glyceric acid1 is also found in nature: in the flowering plants Lotus burttii and L. tenuis.
An early mention in the literature of glyceric acid, presumably as the racemic form DL-glyceric acid2, came in 1861, when Russian chemist Friedrich Konrad Beilstein4, working in Gottingen, Germany, reported on the . He synthesized glyceric acid via the oxidation of glycerol by nitrous acid, a reaction at the University of Utrecht (The Netherlands) in 1876.
In 1903, Alex. McKenzie and Arthur Harden*5 at Victoria University (Manchester, UK), in a treatise on resolving racemic organic acids into their enantiomers, reported that D-glyceric acid could be obtained via the microorganisms on the racemic mixture. Today, D-glyceric acid is by Acetobacter and Gluconacetobacter species, as reported in 2009 by Habe Hiroshi and co-workers at the National Institute of Advanced Industrial Science and Technology (Tokyo).
D-Glyceric acid has several uses, including as a starting material in organic synthesis and as a supplement for activating mitochondrial metabolism in humans. Elevated levels of the compound in the body can indicate metabolic disorders such as D-glyceric aciduria. It is often sold as its sodium salt6.
1. CAS Reg. No. 28305-26-2.
2. CAS Reg. No. 473-81-4.
3. Yes, that Beilstein, founder of the iconic reference Handbuch der organischen Chemie.
4. CAS Reg. No. 13455-01-1.
5. Harden shared the Nobel Prize in Chemistry in 1929.
6. CAS Reg. No. 109175-64-6.
D-Glyceric acid hazard information*
| Hazard class* | GHS code and hazard statement | |
|---|---|---|
| Skin corrosion/irritation, category 2 | H315—Causes skin irritation |  |
| Serious eye damage/eye irritation, category 2A | H319—Causes serious eye irritation | |
*Globally Harmonized System (GHS) of Classification and Labeling of Chemicals. .
Molecules in the News
Benzene1, the Molecule of the Week for July 3, 2023, is a useful solvent; but its use has declined since it was established as a human carcinogen in the 1980s. Recently, however, the molecule appeared in a new setting: outer space. In March, G. Stephen Kocheril*, C. Zagorec-Marks, and H. J. Lewandowski at the University of Colorado (Boulder) tested the theoretical formation of benzene in interstellar space, starting with acetylene. The reaction sequence proceeded smoothly until the phenylium cation2, C6H5+, was produced. But the final purported step, , putting the theory to bed.
Butylated hydroxyanisole3 (BHA) and propylparaben4 (PP) have been used as food preservatives since the 1940s and 1950s, respectively. But in the past 15 years, both molecules have been reported to be dangerous to human health: BHA as a possible carcinogen, and PP as a sex hormone disruptor in females and males. In March, when the state of West Virginia banned seven synthetic food dyes, . California banned PP in 2023.
Nicotine5, the Molecule of the Week for August 20, 2018, is the well-known addictive component of tobacco. In February, Patricia J. Zettler, Theodore L. Wagener, and Micah L. Berman* at Ohio State University (Columbus) asked, “�. In the final days of the Biden administration, the US Food and Drug Administration proposed a substantial reduction in the nicotine content of cigarettes and other tobacco products to reduce their addictiveness. But, because of uncertainty about Trump administration health policy and anticipated strong pushback by the tobacco industry, the proposal is in jeopardy. The authors nevertheless advocated for the reduction to be adopted and urge medical and public health researchers to “submit . . . comments on the proposed rule to supplement the already robust evidence supporting it, countering anticipated arguments against the rule, and identifying ways to prevent industry evasion of a nicotine standard, should one be implemented.�
1. CAS Reg. No. 71-43-2.
2. CAS Reg. No. 17333-73-2.
3. CAS Reg. No. 25013-16-5 (mixture of two isomers).
4. CAS Reg. No. 94-13-3.
5. CAS Reg. No. 54-11-5.
Molecules in the News
MOTW highlights molecules that appear in major news outlets. See this week's edition.
This molecule was suggested by a reader. We present almost all of the molecules suggested by our readers. If you have a molecule you would like us to consider, please send us a message. And thank you for your interest in Molecule of the Week! —Ed.
D-Glyceric acid fast facts
| CAS Reg. No. | 6000-40-4 |
| SciFindern name | Propanoic acid, 2,3-dihydroxy-, (2R)- |
| Empirical formula | C3H6O4 |
| Molar mass | 106.08 g/mol |
| Appearance | Viscous colorless liquid |
| Melting point | <25 ºC |
| Water solubility | Miscible |
, the most authoritative and comprehensive source for chemical information.
Molecule of the Week needs your suggestions!
If your favorite molecule is not in our archive, please send us a message. The molecule can be notable for its current or historical importance or for any quirky reason. Thank you!
Stay Ahead of the Chemistry Curve
Learn how ACS can help you stay ahead in the world of chemistry.
