Benzenesulfonic acid, mono-C11-13-branched alkyl derivs., sodium salts

Biotransformation and kinetics

Administrative data

Endpoint:

biotransformation and kinetics

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Well-documented journal article, no data on GLP.

Data source

Reference

Reference Type:

publication

Title:

Degradation of Alkyl Benzene Sulfonate by Pseudomonas Species

Author:

Horvath, R.S., and Koft, W.B.

Year:

1972

Bibliographic source:

Applied Microbiology, 23 (2), 407-414

Materials and methods

Test guideline

Qualifier:

no guideline followed

Principles of method if other than guideline:

The test substance was added to a basal salts medium consisting of 1.0 g NH4Cl, 1.0 g of Na2HPO4, 0.5 g of KCl, and 0.1 g of MgCl2, per 1 liter water. Various concentrations of glucose, inorganic sulfate, and various carbon and energy sources were also added. A 1% inoculum of Pseudomonas sp. designated HK-1 (10^7 bacteria/ml) was added. This species can cleave the sulfonate moiety, and use it as a source of sulfur. The inoculum was monitored for 32 days. Growth measurements were taken with a Bonet, Maury, and Jouan biophotometer. Metabolic intermediates were isolated and identified by their physical properties or the physical properties of theri carboxylic acid, 3,5 -dinitrobenzoate, or 2,-4 -dinitrophenylhydrazone. ABS was measured using the methylene blue procedure in: American Public Health Association, 1960, Standard methods for the examination of water and wastewater, 11th ed. American Public Health Association, New York.

GLP compliance:

not specified

Type of medium:

aquatic

Test material

Test material information

Constituent 1

Reference substance name:

alkyl benzene sulfonate (BABS Na salt)

IUPAC Name:

alkyl benzene sulfonate (BABS Na salt)

Test material form:

not specified

Results and discussion

Transformation products:

yes

Identity of transformation products

Identity of transformation products 1

No.:

#1

Reference

Reference substance name:

Unnamed

IUPAC name:

t-butanol

Identifier:

common name

Identity:

t-butanol

Identity of transformation products 2

No.:

#2

Reference

Reference substance name:

Unnamed

IUPAC name:

isopropanol

Identifier:

common name

Identity:

isopropanol

Identity of transformation products 3

No.:

#3

Reference

Reference substance name:

Unnamed

IUPAC name:

1-propanol

Identifier:

common name

Identity:

1-propanol

Identity of transformation products 4

No.:

#4

Reference

Reference substance name:

Unnamed

IUPAC name:

2-propenol

Identifier:

common name

Identity:

2-propenol

Identity of transformation products 5

No.:

#5

Reference

Reference substance name:

Unnamed

IUPAC name:

2-hydroxymethyloxirane

Identifier:

common name

Identity:

2-hydroxymethyloxirane

Identity of transformation products 6

No.:

#6

Reference

Reference substance name:

Unnamed

IUPAC name:

propanoic acid

Identifier:

common name

Identity:

propanoic acid

Identity of transformation products 7

No.:

#7

Reference

Reference substance name:

Unnamed

IUPAC name:

methyl phenyl carbinol

Identifier:

common name

Identity:

methyl phenyl carbinol

Identity of transformation products 8

No.:

#8

Reference

Reference substance name:

Unnamed

IUPAC name:

phenyl ethylene glycol

Identifier:

common name

Identity:

phenyl ethylene glycol

Identity of transformation products 9

No.:

#9

Reference

Reference substance name:

Unnamed

IUPAC name:

mandaldehyde

Identifier:

common name

Identity:

mandaldehyde

Identity of transformation products 10

No.:

#10

Reference

Reference substance name:

Unnamed

IUPAC name:

hydroxy(phenyl)acetic acid

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 202-007-6]

CAS number:

90-64-2

Identity:

Benzeneacetic acid, .alpha.-hydroxy-

Identity:

Benzeneacetic acid, ?-hydroxy-

Molecular formula:

C8H8O3

Molecular weight:

152.147

SMILES notation:

OC(C(=O)O)c1ccccc1

InChl:

InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)

Identity of transformation products 11

No.:

#11

Reference

Reference substance name:

Unnamed

IUPAC name:

Phenylmethanol

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 202-859-9]

CAS number:

100-51-6

Identity:

Benzenemethanol

Molecular formula:

C7H8O

Molecular weight:

108.138

SMILES notation:

OCc1ccccc1

InChl:

InChI=1/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

Identity of transformation products 12

No.:

#12

Reference

Reference substance name:

Unnamed

IUPAC name:

Benzaldehyde

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 202-860-4]

CAS number:

100-52-7

Identity:

Benzaldehyde

Identity:

benzaldehyde

Molecular formula:

C7H6O

Molecular weight:

106.122

SMILES notation:

O=Cc1ccccc1

InChl:

InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H

Identity of transformation products 13

No.:

#13

Reference

Reference substance name:

Unnamed

IUPAC name:

benzoic acid

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 200-618-2]

CAS number:

65-85-0

Identity:

Benzoic acid

Molecular formula:

C7H6O2

Molecular weight:

122.121

SMILES notation:

OC(=O)c1ccccc1

InChl:

InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)

Identity of transformation products 14

No.:

#14

Reference

Reference substance name:

Unnamed

IUPAC name:

phenol

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 203-632-7]

CAS number:

108-95-2

Molecular formula:

C6H6O

Molecular weight:

94.11

SMILES notation:

Oc1ccccc1

InChl:

InChI=1/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H

Identity of transformation products 15

No.:

#15

Reference

Reference substance name:

Unnamed

IUPAC name:

catechol

Identifier:

common name

Identity:

catechol

Any other information on results incl. tables

Amount of ABS (mmoles/L)	Amount dry cell wt. (mg/L)
2.870	378
1.430	243.6
0.715	151.2
0.287	92.4

The above growth results shows that the Pseudomonas sp. HK-1 is capable of growing in ABS media. 4 mmoles of adenosine triphosphate per mmole of ABS degraded was obtained by the Pseudomonas. Degradation begins with the oxidation and then hydrolysis of the branched side chain into t-butanol and isopropanol. The ispropanol further degrades to 1 -propanol, to 2 -propenol, to 2 -hydroxymethyloxirane, and finally to propanoic acid. The sulfonate group cleaves, and the branced side chain eventually degrades to the point that methyl phenyl carbinol is formed. The methyl phenyl carbinol degrades by further hydrolysis and oxidation to phenyl ethylene glycol, to mandaldehyde, to mandelic acid, to benzyl alcohol, to benzaldehyde, to benzoic acid, to phenol, and possibly to catechol.

Applicant's summary and conclusion

Conclusions:

The ultimate degradation products of ABS are t-butanol, propanoic acid, phenol, and catechol.

Executive summary:

The degradation of BABS Na salt was monitored for 32 days. The ultimate degradation products are t-butanol, propanoic acid, phenol, and catechol. The biodegradation pathway of BABS Na salt (branched alkyl benzene sulfonate) was similar to that of linear alkyl benzene sulfonate (LAS).