E235 (Natamycin) is a natural polyene tetraene antimicrobial peptide that is obtained during the fermentation of strains of the Gram-positive bacterium Streptomyces natalensis found in soil.

It appears in the form of a white powder.

What it is used for and where

Medical

It is an antifungal used in many diseases such as fungal keratitis that can develop into infectious keratitis (1)

Food

It has the function of preventing fungal growth at low pH, low humidity and low temperature in food products. However, it is incompatible with peroxyacetic acid, resulting in reduced effectiveness against green mould (2).

Ingredient listed in the European food additives list as E235, preservative.

Cosmetics

It is an ingredient used as an antimicrobial and antifungal.

Antimicrobial agent. This ingredient is able to suppress or inhibit the growth and replication of a broad spectrum of microorganisms such as bacteria, fungi and viruses by making the stratum corneum temporarily bactericidal and fungicidal.

Preservative. Any product containing organic, inorganic compounds, water, needs to be preserved from microbial contamination. Preservatives act against the development of harmful microorganisms and against oxidation of the product.

Natamycin studies

Molecular Formula      C₃₃H₄₇O₁₃N    C₃₃H₄₇NO₁₃

Molecular Weight      665.7

CAS  7681-93-8

UNII    8O0C852CPO

EC Number   231-683-5

DSSTox ID  

IUPAC  (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

InChl=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1

InChl Key      NCXMLFZGDNKEPB-FFPOYIOWSA-N

SMILES  CC1CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC3C(O3)C=CC(=O)O1)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O

MDL number  MFCD00135085

PubChem Substance ID    329754196

RTECS  TK3325000

NCI    C47634

RXCUI  7268   

Metabolomics Workbench   98963      

Synonyms:

• Pimaricin
• delvocid
• antibiotic A 5283
• mycophyt
• delvopos
• Synogil

References_________________________________________________________________________

(1) Prajna NV, Radhakrishnan N. Intrastromal natamycin: A well-aimed arrow in a difficult battle. Indian J Ophthalmol. 2021 Oct;69(10):2565. doi: 10.4103/ijo.IJO_775_21.

(2) Chen D, Förster H, Nguyen K, Adaskaveg JE. Organic Acid Sanitizers for Natamycin and Other Fungicides in Recirculating Application Systems for Citrus Postharvest Decay Management. Plant Dis. 2021 Oct;105(10):2907-2913. doi: 10.1094/PDIS-01-21-0227-RE.