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S3523

Surfactin

Name: Surfactin
Brand: SIGMA

from Bacillus subtilis, ≥98.0% (HPLC)

Synonym(s):

surfactin C

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About This Item

Empirical Formula (Hill Notation):

C₅₃H₉₃N₇O₁₃

CAS Number:

24730-31-2

Molecular Weight:

1036.34

UNSPSC Code:

51102829

PubChem Substance ID:

24899562

NACRES:

NA.85

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Properties

biological source

Bacillus subtilis

Quality Segment

200

description

zwitterionic

assay

≥98.0% (HPLC)

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)

color

white to faint yellow

CMC

7.5-20 μmol/L (depending on methods)

solubility

ethanol: soluble 10 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, fungi, mycoplasma, neoplastics, viruses

mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

CC(C)CCCCCCCCC[C@@H]1CC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)O1

InChI

1S/C53H93N7O13/c1-30(2)20-18-16-14-13-15-17-19-21-36-28-43(61)54-37(22-23-44(62)63)47(66)55-38(24-31(3)4)48(67)57-40(26-33(7)8)51(70)60-46(35(11)12)52(71)58-41(29-45(64)65)50(69)56-39(25-32(5)6)49(68)59-42(27-34(9)10)53(72)73-36/h30-42,46H,13-29H2,1-12H3,(H,54,61)(H,55,66)(H,56,69)(H,57,67)(H,58,71)(H,59,68)(H,60,70)(H,62,63)(H,64,65)/t36-,37+,38+,39-,40-,41+,42+,46+/m1/s1

InChI key

NJGWOFRZMQRKHT-WGVNQGGSSA-N

Description

General description

Chemical structure: peptide

Application

Surfactin is used as a surfactant to mediate flux of mono-and divalent cations, such as calcium, across lipid bilayer membranes. It is also used to study antitumor activity, activity against enveloped viruses, activity against the protoplast of Bacillus megaterium and the activity against Mycoplasma.

Biochem/physiol Actions

Surfactin is a lipopeptide antibiotic that is composed of one β-hydroxy fatty acid, which has a long fatty acid moiety, and seven amino acids. Three of them have D configurations. It is a powerful biosurfactant that causes lysis of erythrocytes and bacteria. It is also a clotting inhibitor. Surfactin is thought to disrupt or disintegrate membranes via physicochemical interaction with the membranes.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c