Reuterin | CAS#2134-29-4 | Antibacterial activity

MedKoo Cat#: 112030 | Name: Reuterin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Reuterin is a glycerol metabolite originally isolated from L. reuteri, a bacteria found in the intestines of humans, that has antibacterial activity. It is produced by L. reuteri during exposure to live or UV-killed E. coli. Reuterin is active against E. coli and several species of Bacteroides, Bifidobacterium, and Eubacterium (MICs = 1.9-15 mM) as well as C. difficile and B. vulgatus (MICs = <1.9 mM for both). It enhances increases in the production of reactive oxygen species (ROS) and cell death induced by vancomycin or metronidazole in C. difficile when used at a concentration of 2.5 mM. Reuterin alters the bacterial composition of, and volatile organic compounds (VOCs) produced by, the mouse fecal microbiome.

Chemical Structure

Reuterin

CAS#2134-29-4

Theoretical Analysis

MedKoo Cat#: 112030

Name: Reuterin

CAS#: 2134-29-4

Chemical Formula: C3H6O2

Exact Mass: 74.0368

Molecular Weight: 74.08

Elemental Analysis: C, 48.64; H, 8.16; O, 43.19

Price and Availability

Size	Price	Availability
25mg	USD 260.00	2 Weeks
50mg	USD 510.00	2 Weeks
100mg	USD 790.00	2 Weeks
250mg	USD 1,190.00	2 Weeks

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Related CAS #

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Synonym

Reuterin; 3-HPA; 3-Hydroxypropionaldehyde; β-Hydroxypropionaldehyde; 3HPA; 3Hydroxypropionaldehyde; βHydroxypropionaldehyde; 3 HPA; 3 Hydroxypropionaldehyde β Hydroxypropionaldehyde

IUPAC/Chemical Name

3-hydroxypropanal

InChi Key

AKXKFZDCRYJKTF-UHFFFAOYSA-N

InChi Code

InChI=1S/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2

SMILES Code

O=CCCO

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	337.47
	DMSO	20.0	269.98
	Ethanol	16.0	215.98
	PBS (pH: 7.2)	5.0	67.49

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 74.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Bell HN, Rebernick RJ, Goyert J, Singhal R, Kuljanin M, Kerk SA, Huang W, Das NK, Andren A, Solanki S, Miller SL, Todd PK, Fearon ER, Lyssiotis CA, Gygi SP, Mancias JD, Shah YM. Reuterin in the healthy gut microbiome suppresses colorectal cancer growth through altering redox balance. Cancer Cell. 2022 Feb 14;40(2):185-200.e6. doi: 10.1016/j.ccell.2021.12.001. Epub 2021 Dec 23. PMID: 34951957; PMCID: PMC8847337. 2: Engevik MA, Danhof HA, Shrestha R, Chang-Graham AL, Hyser JM, Haag AM, Mohammad MA, Britton RA, Versalovic J, Sorg JA, Spinler JK. Reuterin disrupts Clostridioides difficile metabolism and pathogenicity through reactive oxygen species generation. Gut Microbes. 2020 Nov 9;12(1):1788898. doi: 10.1080/19490976.2020.1795388. PMID: 32804011; PMCID: PMC7524292. 3: Rodrigues FJ, Cedran MF, Bicas JL, Sato HH. Reuterin-producing Limosilactobacillus reuteri: Optimization of in situ reuterin production in alginate-based filmogenic solutions. Curr Res Food Sci. 2021 Nov 27;4:926-931. doi: 10.1016/j.crfs.2021.11.013. PMID: 34927088; PMCID: PMC8646958. 4: Kumar N, Kumar V, Waheed SM, Pradhan D. Efficacy of Reuterin and Bacteriocins Nisin and Pediocin in the Preservation of Raw Milk from Dairy Farms. Food Technol Biotechnol. 2020 Dec;58(4):359-369. doi: 10.17113/ftb.58.04.20.6728. PMID: 33505199; PMCID: PMC7821776. 5: Rodríguez-Mínguez E, Huedo P, Langa S, Peirotén Á, Landete JM, Medina M, Arqués JL. Genome Sequence of the Reuterin-Producing Strain Limosilactobacillus reuteri INIA P572. Microbiol Resour Announc. 2021 Dec 9;10(49):e0098821. doi: 10.1128/MRA.00988-21. Epub 2021 Dec 9. PMID: 34881975; PMCID: PMC8656388. 6: Asare PT, Zurfluh K, Greppi A, Lynch D, Schwab C, Stephan R, Lacroix C. Reuterin Demonstrates Potent Antimicrobial Activity Against a Broad Panel of Human and Poultry Meat Campylobacter spp. Isolates. Microorganisms. 2020 Jan 6;8(1):78. doi: 10.3390/microorganisms8010078. PMID: 31935889; PMCID: PMC7022665. 7: Mu Q, Tavella VJ, Luo XM. Role of Lactobacillus reuteri in Human Health and Diseases. Front Microbiol. 2018 Apr 19;9:757. doi: 10.3389/fmicb.2018.00757. PMID: 29725324; PMCID: PMC5917019. 8: Das NK, Schwartz AJ, Barthel G, Inohara N, Liu Q, Sankar A, Hill DR, Ma X, Lamberg O, Schnizlein MK, Arqués JL, Spence JR, Nunez G, Patterson AD, Sun D, Young VB, Shah YM. Microbial Metabolite Signaling Is Required for Systemic Iron Homeostasis. Cell Metab. 2020 Jan 7;31(1):115-130.e6. doi: 10.1016/j.cmet.2019.10.005. Epub 2019 Nov 7. PMID: 31708445; PMCID: PMC6949377. 9: Castellani C, Obermüller B, Kienesberger B, Singer G, Peterbauer C, Grabherr R, Mayrhofer S, Klymiuk I, Horvath A, Stadlbauer V, Russmayer H, Miekisch W, Fuchs P, Till H, Heinl S. Production, Storage Stability, and Susceptibility Testing of Reuterin and Its Impact on the Murine Fecal Microbiome and Volatile Organic Compound Profile. Front Microbiol. 2021 Jul 30;12:699858. doi: 10.3389/fmicb.2021.699858. PMID: 34394042; PMCID: PMC8361477. 10: Martín-Cabrejas I, Langa S, Gaya P, Rodríguez E, Landete JM, Medina M, Arqués JL. Optimization of reuterin production in cheese by Lactobacillus reuteri. J Food Sci Technol. 2017 Apr;54(5):1346-1349. doi: 10.1007/s13197-017-2563-2. Epub 2017 Mar 3. PMID: 28416886; PMCID: PMC5380638. 11: Mishra SK, Malik RK, Panwar H, Barui AK. Microencapsulation of reuterin to enhance long-term efficacy against food-borne pathogen Listeria monocytogenes. 3 Biotech. 2018 Jan;8(1):23. doi: 10.1007/s13205-017-1035-8. Epub 2017 Dec 18. PMID: 29276661; PMCID: PMC5735039. 12: Soltani S, Couture F, Boutin Y, Ben Said L, Cashman-Kadri S, Subirade M, Biron E, Fliss I. In vitro investigation of gastrointestinal stability and toxicity of 3-hyrdoxypropionaldehyde (reuterin) produced by Lactobacillus reuteri. Toxicol Rep. 2021 Mar 31;8:740-746. doi: 10.1016/j.toxrep.2021.03.025. PMID: 33868958; PMCID: PMC8042431. 13: Vimont A, Fernandez B, Ahmed G, Fortin HP, Fliss I. Quantitative antifungal activity of reuterin against food isolates of yeasts and moulds and its potential application in yogurt. Int J Food Microbiol. 2019 Jan 16;289:182-188. doi: 10.1016/j.ijfoodmicro.2018.09.005. Epub 2018 Sep 6. PMID: 30253311. 14: Zhang Z, Wang K, Oh JH, Zhang S, van Pijkeren JP, Cheng CC, Ren D, Wei H, Gänzle MG, Walter J. A Phylogenetic View on the Role of Glycerol for Growth Enhancement and Reuterin Formation in Limosilactobacillus reuteri. Front Microbiol. 2020 Dec 21;11:601422. doi: 10.3389/fmicb.2020.601422. PMID: 33408707; PMCID: PMC7779471. 15: Fujiwara N, Murakami K, Nakao M, Toguchi M, Yumoto H, Amoh T, Hirota K, Matsuo T, Sano S, Ozaki K, Miyake Y. Novel reuterin-related compounds suppress odour by periodontopathic bacteria. Oral Dis. 2017 May;23(4):492-497. doi: 10.1111/odi.12638. Epub 2017 Mar 9. PMID: 28083982. 16: Schaefer L, Auchtung TA, Hermans KE, Whitehead D, Borhan B, Britton RA. The antimicrobial compound reuterin (3-hydroxypropionaldehyde) induces oxidative stress via interaction with thiol groups. Microbiology (Reading). 2010 Jun;156(Pt 6):1589-1599. doi: 10.1099/mic.0.035642-0. Epub 2010 Feb 11. PMID: 20150236; PMCID: PMC7336520. 17: Greppi A, Asare PT, Schwab C, Zemp N, Stephan R, Lacroix C. Isolation and Comparative Genomic Analysis of Reuterin-Producing Lactobacillus reuteri From the Chicken Gastrointestinal Tract. Front Microbiol. 2020 Jun 4;11:1166. doi: 10.3389/fmicb.2020.01166. PMID: 32670217; PMCID: PMC7326114. 18: Bennett S, Ben Said L, Lacasse P, Malouin F, Fliss I. Susceptibility to Nisin, Bactofencin, Pediocin and Reuterin of Multidrug Resistant Staphylococcus aureus, Streptococcus dysgalactiae and Streptococcus uberis Causing Bovine Mastitis. Antibiotics (Basel). 2021 Nov 19;10(11):1418. doi: 10.3390/antibiotics10111418. PMID: 34827356; PMCID: PMC8614789. 19: Asare PT, Greppi A, Stettler M, Schwab C, Stevens MJA, Lacroix C. Decontamination of Minimally-Processed Fresh Lettuce Using Reuterin Produced by Lactobacillus reuteri. Front Microbiol. 2018 Jul 4;9:1421. doi: 10.3389/fmicb.2018.01421. PMID: 30022970; PMCID: PMC6040215. 20: Fernández-Cruz ML, Martín-Cabrejas I, Pérez-Del Palacio J, Gaya P, Díaz- Navarro C, Navas JM, Medina M, Arqués JL. In vitro toxicity of reuterin, a potential food biopreservative. Food Chem Toxicol. 2016 Oct;96:155-9. doi: 10.1016/j.fct.2016.08.002. Epub 2016 Aug 2. PMID: 27495826.