DL-Methionine

Inquiry

Cat Number

API59518

CAS Number

59-51-8

If you have any other questions, please contact our experts.

Product Detail Description Scientific Support Customer Q&A

CAS Number

59-51-8

EINECS

200-432-1

Synonyms

Racemethionine; Acimetion; Lobamine

Molecular Formula

C5H11NO2S

Molecular Weight

149.21

Smiles

CSCCC(C(=O)O)N

Appearance

White crystalline platelets or powder

Melting Point

281 ℃

Boiling Point

300 ℃

Standard

USP/EP

General Description

DL-Methionine is a racemic mixture of the D-form and L-form of methionine. Although the L-form is the naturally occurring form found in proteins, organisms efficiently metabolize D-Methionine to L-Methionine, rendering the DL-mixture a superior and economical form of supplementation. DL-Methionine is used as a building block for protein synthesis and is utilized as a precursor for many biochemical compounds.

Mechanism of Action

DL-Methionine acts as a major methyl donor to various transmethylation reactions after being converted to S-adenosylmethionine (SAMe). These methyl groups are utilized in the biosynthesis of DNA, neurotransmitters, phospholipids, cysteine, taurine, and glutathione. When metabolized in the kidneys, methionine produces sulfuric acid, giving methionine its acidifying effect on the urine.

Application

DL-Methionine is a common feed additive for poultry and swine as it is often-times the first limiting amino acid needed for growth and feathering. DL-Methionine has also been incorporated into prescription dog and cat diets formulated to acidify the urine to prevent the formation of struvite uroliths. DL-Methionine finds pharmaceutical and nutraceutical applications as a lipotropic factor to promote liver health and detoxification. It can also be used in parenteral nutrition as well as in hair, skin and nail formulas.

The impact of dietary DL-methionine (DL-Met) supplementation (0.3%) in breeding pigeons was investigated on intestinal development in squabs. DL-Met improves the average daily gain and lowers mortality compared to control squabs. Morphology of the intestine is increased with DL-Met supplementation by upregulating villus height and the villus-to-crypt ratio, specifically in the duodenum. DL-Met improves tight junction protein expression including ZO-1 and Claudin-1. These data support DL-Met improve intestinal barrier function in the intestine of squabs.
Treatment with DL-Met increased expression of cell proliferation and differentiation markers Ki67, PCNA, and Villin in the small intestine. PepT1 peptide transporter expression is upregulated by DL-Met treatment. Supplementation of DL-Met activates the Wnt/β-catenin signaling pathway, suggested by increased expression of Frizzled 7, p-GSK-3β, active β-catenin and downstream target genes including TCF4, c-Myc, and Cyclin D1. Molecular docking indicated DL-Met may directly bind with FZD7 to induce Wnt signaling.

Fig. 1 DL-methionine intensifies FZD7-mediated Wnt/b-catenin signaling activity. (Zhong C.; et al. 2022)

References

Zhong C.; et al. DL-methionine and DL-methionyl-DL-methionine increase intestinal development and activate Wnt/β-catenin signaling activity in domestic pigeons (Columba livia). Poultry Science, 2022, 101(3): 101644.

What is the difference between L-Methionine and DL-Methionine?

L-Methionine refers to the naturally occurring isomer while DL-Methionine is synthetically produced as a mixture of both enantiomers.

Will DL-Methionine dissolve in water?

DL-Methionine is slightly soluble in water; it is soluble in acidic or alkaline solutions.

Does DL Methionine smell?

DL-Methionine, similar to most sulfur-containing amino acids, will have a characteristic mild sulfurous or cabbage smell.

How should DL Methionine be stored?

Store in a cool, dry place in tightly closed containers.