1,3-Dihydroxyacetone
[CAS# 96-26-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: 1,3-Dihydroxyacetone
• Synonyms: 1,3-Dihydroxy-2-propanone; Dihydroxyacetone; Glycerone
• Molecular Formula: C₃H₆O₃
• Molecular Weight: 90.08
• CAS Registry Number: 96-26-4
• EC Number: 202-494-5
• FEMA: 4033
• SMILES: C(C(=O)CO)O

Properties

• Water solubility: >250 g/L (20 ºC)
• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 80 ºC (Expl.)
• Index of Refraction: 1.455, Calc.^*
• Boiling Point: 213.7±15.0 ºC (760 mmHg), Calc.^*
• Flash Point: 97.3±16.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

1,3-Dihydroxyacetone, also known as DHA, is an organic compound with the chemical formula C3H6O3. It is a simple carbohydrate that is widely recognized for its use in cosmetic and dermatological products, particularly in sunless tanning products. DHA was first synthesized in the mid-20th century and is derived from glycerol, which serves as its precursor. DHA is a colorless, odorless liquid under standard conditions and is highly soluble in water.

The compound's discovery and use date back to the 1920s, when it was first identified for its potential in the tanning industry. DHA gained prominence in the 1960s and 1970s due to its application in self-tanning formulations. Unlike other tanning agents that require exposure to UV radiation, DHA reacts with the amino acids in the outer layer of the skin to produce a browning effect, mimicking the appearance of a natural tan. This reaction occurs through a process known as the Maillard reaction, which is a non-enzymatic reaction between a reducing sugar, like DHA, and an amino acid. The resulting color change is temporary, usually lasting for several days, as the skin cells are naturally shed and replaced.

In addition to its widespread use in self-tanning products, DHA has several other notable applications. It is commonly used as an ingredient in medical and cosmetic formulations, where it serves both functional and aesthetic roles. For example, DHA is included in formulations for various skincare products due to its ability to provide a temporary tan without the need for UV exposure, which can cause skin damage and increase the risk of skin cancer.

DHA is also employed in the food and beverage industry. It is sometimes used as a browning agent in foods such as baked goods, providing a desirable color and appearance. Additionally, DHA has been incorporated into certain beverages and products as a flavoring agent or coloring agent. While it is not as commonly used in the food industry as in cosmetics, its role in these applications is nonetheless significant.

Another area of interest for DHA is its potential in the pharmaceutical industry. Researchers have investigated DHA as a potential precursor for the synthesis of other bioactive molecules. Additionally, it has been studied for its ability to provide benefits when used in wound care products and for its possible roles in the treatment of certain skin conditions.

DHA’s safety has been extensively studied, particularly in the context of its use in cosmetics and personal care products. It is considered safe for topical use in concentrations typically found in commercial tanning products. The compound does not penetrate deeply into the skin, and the browning effect is temporary and confined to the outermost layers of skin cells. However, it is important to note that while DHA has been deemed safe for external use, it should not be ingested, and its use in the vicinity of mucous membranes or eyes should be avoided.

Furthermore, DHA is also recognized for its potential use in medical imaging and as a component in certain chemical synthesis processes, though these applications are less widespread. Its ability to react with other compounds and its relatively simple molecular structure make it a useful intermediate in organic synthesis.

1,3-Dihydroxyacetone is a versatile and important compound with several established applications. Its primary use remains in the cosmetic industry, particularly for self-tanning products, but its uses extend to food processing, pharmaceuticals, and other specialized industries. The compound’s safety profile and well-understood chemistry have contributed to its continued use in these areas.

References

2024. Calcination Temperature Impacting the Structure and Activity of CuAl Catalyst in Aqueous Glycerol Hydrogenolysis to 1,2-Propanediol. Topics in Catalysis, 67(19-20).
DOI: 10.1007/s11244-024-02032-5

2024. Effective multi-biocatalyst system with reusable NADH for transformation of glycerol to value-added dihydroxyacetone. Chemical and Biological Technologies in Agriculture, 11(1).
DOI: 10.1186/s40538-024-00666-x

2024. Precision-cut liver slices as an ex vivo model to assess impaired hepatic glucose production. Communications Biology, 7(1).
DOI: 10.1038/s42003-024-07070-z