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52-39-1

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52-39-1 Usage

Description

Aldosterone is a mineralocorticosteroid that takes part in the regulation of electrolytic balance in the organism. Aldosterone lowers excretion of sodium ions from the body, thus increasing their reabsorption and increasing secretion of potassium ions in renal tubules. Being a competitive antagonist of aldosterone, spironlactone blocks aldosterone receptors, thus increasing excretion of sodium, chloride, and corresponding equivalents of water with urine, thus retaining the amount of potassium ions in the organism. Spironolactone is used both individually as well as in combination with thiazides, since it lowers kaliuresis caused by thiazide diuretics.

Chemical Properties

White Solid

Originator

Aldosterone ,Sigma Chemical Company

Uses

Different sources of media describe the Uses of 52-39-1 differently. You can refer to the following data:
1. A labelled adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water. Biologically active aldosterone isomer; a mineralocorticoid produced by the adrenal cortex that induces urinary excretion of K+ and renal re
2. The d-isomer of aldosterone is considered to be the biologically active isomer.
3. Labelled Aldosterone. Aldosterone is an adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water. Biologically active aldosterone isomer; a mineralocorticoid pr oduced by the adrenal cortex that induces urinary excretion of K+ and renal reabsorptioon of Na+. Exists as an equilibrium mixture of the aldehyde and the hemiacetal.
4. hypnotic, anastethic

Definition

Different sources of media describe the Definition of 52-39-1 differently. You can refer to the following data:
1. ChEBI: A pregnane-based steroidal hormone produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland, and acts on the distal tubules and collecting ducts of the kidney to cause the conservation of sodium, secretion of potassium, i creased water retention, and increased blood pressure. The overall effect of aldosterone is to increase reabsorption of ions and water in the kidney.
2. aldosterone: A hormone producedby the adrenal glands that controlsexcretion of sodium by the kidneysand thereby maintains the balance ofsalt and water in the body fluids.

Therapeutic Function

Mineralocorticoid

Biological Functions

Aldosterone, produced by the adrenal cortex, acts at epithelial cells in the distal tubule of the nephron to increase the reabsorption of sodium and is therefore considered an important hormone in the regulation of electrolyte balance. Aldosterone exerts its effects at the nephron through mineralocorticoid receptors, which translocate to the nucleus upon aldosterone binding and exert genomic effects leading to increased sodium reabsorption. In addition to the epithelial effects of aldosterone at mineralocorticoid receptors, nonepithelial cells, including cardiac muscle and vascular smooth muscle cells and cells in the brain, can respond to aldosterone and result in left ventricular hypertrophy, cardiac and vascular fibrosis, and stimulation of sympathetic nervous system activity. Spironolactone (Aldactone), an antagonist of the aldosterone mineralocorticoid receptor, is used to treat primary aldosteronism, essential hypertension, and congestive heart failure. In the treatment of hypertension resulting from adrenal adenoma (primary aldosteronism) and in patients with essential hypertension, spironolactone lowers blood pressure primarily through blockade of epithelial mineralocorticoid receptors in the kidney, reductions in sodium and water reabsorption, and diuresis.The use of spironolactone in the treatment of essential hypertension is typically restricted to patients who do not respond appropriately to other agents and is often used in combination drug therapy. In large-scale clinical trials in patients with severe heart failure, administration of spironolactone markedly reduced morbidity and mortality without reducing blood pressure. Spironolactone is used to treat patients with moderate to severe heart failure who exhibit symptoms and ventricular dysfunction despite treatment with an ACE inhibitor or a diuretic. Adverse effects of spironolactone therapy include hyperkalemia, gastrointestinal problems, gynecomastia (breast enlargement in males), and impotence. Gynecomastia and impotence arising from spironolactone treatment are results of significant blockade of the androgen and mineralocorticoid receptors.Novel selective mineralocorticoid receptor antagonists, such as eplerenone, are in clinical trials.

Health Hazard

Aldosterone(Aldocortin; electrocortin; mineralocorticoid; 18-oxocorticosterone): (1)Maintenance of normal electrolyte blood balances;(2)Prolongs survival of adrenalectomized animals;(3)Accelerates gluconeogenesis;(4)Regulates kidney function.

Synthesis

Aldosterone, 11β,21-dihydroxypregn-4-en-2,18,20-trione (27.2.4), is synthesized from 21-O-acetylcorticosterone, which when reacted with nitrosyl chloride in pyridine gives the nitrite 27.2.1. When photochemically irradiated, this compound is transformed to the oxime 27.2.2, which is hydrolyzed by nitrous acid and forms the semiacetal 27.2.3, which is an acetate of the desired aldosterone. Alkaline hydrolysis of the acetyl group of this compound leads to the desired aldosterone (27.2.4) .

Purification Methods

Crystallise aldosterone from aqueous acetone. It exists in solution as an equilibrium mixture of free aldehyde and its cyclic hemiacetal, favouring the hemiacetal. The 21-acetate crystallises from Me2CO/Et2O or CH2Cl2/EtOAc and has m 198-199o, [] D +121.7o (c 0.7, CHCl3). [Barton et al. J Chem Soc Perkin Trans 1 2243 1975, Beilstein 8 IV 3491.]

Check Digit Verification of cas no

The CAS Registry Mumber 52-39-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 2 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 52-39:
(4*5)+(3*2)+(2*3)+(1*9)=41
41 % 10 = 1
So 52-39-1 is a valid CAS Registry Number.
InChI:InChI=1/C21H28O5/c1-20-7-6-12(23)8-11(20)2-3-13-14-4-5-15(16(24)10-22)21(14)9-17(18(13)20)26-19(21)25/h8,13-15,17-19,22,25H,2-7,9-10H2,1H3

52-39-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name aldosterone

1.2 Other means of identification

Product number -
Other names Pregn-4-en-18-al, 11,21-dihydroxy-3,20-dioxo-, (11β)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:52-39-1 SDS

52-39-1Synthetic route

3,3;20,20-bis-ethanediyldioxy-11β,21-dihydroxy-pregn-5-en-18-al
124537-57-1

3,3;20,20-bis-ethanediyldioxy-11β,21-dihydroxy-pregn-5-en-18-al

aldosterone
52-39-1

aldosterone

Conditions
ConditionsYield
With hydrogenchloride
Pregnenolone
145-13-1

Pregnenolone

A

Corticosterone
50-22-6

Corticosterone

B

aldosterone
52-39-1

aldosterone

C

18,21-dihydroxy-4-pregnen-3,20-dione
10385-97-4

18,21-dihydroxy-4-pregnen-3,20-dione

Conditions
ConditionsYield
With air; dibutyric cyclic AMP; NaHCO3 buffer; normal male Sprague-Dawley rat adrenal glands after feeding for 72 h with 1 percent NaCl at 37℃; for 3h; Product distribution; tritium labeled study;
aldosterone 21-acetate
297-91-6

aldosterone 21-acetate

aldosterone
52-39-1

aldosterone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: chromium (VI)-oxide; acetic acid
2: methanol; concentrated aqueous hydrochloric acid
3: ethylene glycol; toluene-4-sulfonic acid / 0.2 Torr
4: dioxane; lithium alanate; diethyl ether
5: aqueous HCl
View Scheme
11β,21-dihydroxy-3,20-dioxo-pregn-4-en-18-oic acid-11-lactone
2507-89-3

11β,21-dihydroxy-3,20-dioxo-pregn-4-en-18-oic acid-11-lactone

aldosterone
52-39-1

aldosterone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethylene glycol; toluene-4-sulfonic acid / 0.2 Torr
2: dioxane; lithium alanate; diethyl ether
3: aqueous HCl
View Scheme
21-acetoxy-11β-hydroxy-3,20-dioxo-pregn-4-en-18-oic acid-lactone
3329-80-4

21-acetoxy-11β-hydroxy-3,20-dioxo-pregn-4-en-18-oic acid-lactone

aldosterone
52-39-1

aldosterone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methanol; concentrated aqueous hydrochloric acid
2: ethylene glycol; toluene-4-sulfonic acid / 0.2 Torr
3: dioxane; lithium alanate; diethyl ether
4: aqueous HCl
View Scheme
3,3;20,20-bis-ethanediyldioxy-11β,21-dihydroxy-pregn-5-en-18-oic acid-11-lactone
86698-82-0

3,3;20,20-bis-ethanediyldioxy-11β,21-dihydroxy-pregn-5-en-18-oic acid-11-lactone

aldosterone
52-39-1

aldosterone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dioxane; lithium alanate; diethyl ether
2: aqueous HCl
View Scheme
C21H30O2*C42H70O35
117824-25-6

C21H30O2*C42H70O35

A

11-alpha-hydroxyprogesterone
80-75-1

11-alpha-hydroxyprogesterone

B

20-hydroxy-pregnan-18-oic acid

20-hydroxy-pregnan-18-oic acid

C

aldosterone
52-39-1

aldosterone

Conditions
ConditionsYield
With potassium dihydrogenphosphate; magnesium sulfate heptahydrate; L-asparagine; D-glucose In ethanol; water at 30℃; for 72h; pH=5.5; Time; Concentration; Microbiological reaction; Overall yield = 62.95 %Chromat.;A 48.25 %Chromat.
B 6.84 %Chromat.
C 7.86 %Chromat.
Progesterone
57-83-0

Progesterone

A

11-alpha-hydroxyprogesterone
80-75-1

11-alpha-hydroxyprogesterone

B

20-hydroxy-pregnan-18-oic acid

20-hydroxy-pregnan-18-oic acid

C

aldosterone
52-39-1

aldosterone

Conditions
ConditionsYield
With potassium dihydrogenphosphate; magnesium sulfate heptahydrate; L-asparagine; D-glucose; β‐cyclodextrin In ethanol; water at 30℃; for 48h; pH=5.5; Solvent; Reagent/catalyst; Time; Concentration; Microbiological reaction; Overall yield = 87.15 %Chromat.;A 71.33 %Chromat.
B 8.58 %Chromat.
C 7.24 %Chromat.
aldosterone
52-39-1

aldosterone

4-bromoaldosterone

4-bromoaldosterone

Conditions
ConditionsYield
With oxone; triethylamine; sodium bromide In tetrahydrofuran; water at 20℃; for 3h;83%
aldosterone
52-39-1

aldosterone

C21H27ClO4

C21H27ClO4

Conditions
ConditionsYield
Stage #1: aldosterone With dmap; methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 1h;
Stage #2: With lithium chloride In N,N-dimethyl-formamide at 60℃; for 2h;
80.9%
Stage #1: aldosterone With dmap; methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 1h;
Stage #2: With lithium chloride In N,N-dimethyl-formamide at 60℃; for 2h;
80.9%
aldosterone
52-39-1

aldosterone

diethyl malonate
105-53-3

diethyl malonate

C28H40O9

C28H40O9

Conditions
ConditionsYield
With sodium ethanolate In tetrahydrofuran at 0 - 20℃; for 6h; Schlenk technique;57%
aldosterone
52-39-1

aldosterone

(18Ξ)-11β,18-epoxy-18-hydroxy-3-oxo-androst-4-ene-17β-carboxylic acid-lactone
21966-75-6

(18Ξ)-11β,18-epoxy-18-hydroxy-3-oxo-androst-4-ene-17β-carboxylic acid-lactone

Conditions
ConditionsYield
With methanol; sodium periodate
aldosterone
52-39-1

aldosterone

acetic anhydride
108-24-7

acetic anhydride

Aldosterone 18,21-diacetate
3329-79-1

Aldosterone 18,21-diacetate

Conditions
ConditionsYield
With pyridine
aldosterone
52-39-1

aldosterone

A

2C21H27O8S(1-)*2H4N(1+)*3H2O

2C21H27O8S(1-)*2H4N(1+)*3H2O

B

aldosterone 21-ammonium sulphate

aldosterone 21-ammonium sulphate

C

2C21H27O8S(1-)*2H4N(1+)*3H2O

2C21H27O8S(1-)*2H4N(1+)*3H2O

D

2C21H27O8S(1-)*2H4N(1+)*3H2O

2C21H27O8S(1-)*2H4N(1+)*3H2O

Conditions
ConditionsYield
With triethylamine sulfur trioxide In pyridine at 20℃; for 4h; Yield given. Title compound not separated from byproducts;
aldosterone
52-39-1

aldosterone

A

20β-dihydroaldosterone 18,11β-hemiacetal

20β-dihydroaldosterone 18,11β-hemiacetal

B

C21H28(2)H2O5

C21H28(2)H2O5

Conditions
ConditionsYield
With Tris-HCl buffer; 1,4-dihydronicotinamide adenine dinucleotide for 7h; Ambient temperature; 3α,20β-hydroxysteroid dehydrogenase;
aldosterone
52-39-1

aldosterone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

aldosterone 21-TBDMS ether
113249-21-1

aldosterone 21-TBDMS ether

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane for 0.166667h;30 mg
aldosterone
52-39-1

aldosterone

A

11β,21-dihydroxy-3,20-dioxo-5α-pregnan-18-al
6251-71-4

11β,21-dihydroxy-3,20-dioxo-5α-pregnan-18-al

B

11β,21-dihydroxy-3,20-dioxo-5β-pregnan-18-al
7305-52-4

11β,21-dihydroxy-3,20-dioxo-5β-pregnan-18-al

C

3α,11β,21-trihydroxy-20-oxo-5β-pregnan-18-al
2527-07-3

3α,11β,21-trihydroxy-20-oxo-5β-pregnan-18-al

D

3α,11β,21-trihydroxy-20-oxo-5α-pregnan-18-al

3α,11β,21-trihydroxy-20-oxo-5α-pregnan-18-al

E

3β,11β,21-trihydroxy-20-oxo-5α-pregnan-18-al

3β,11β,21-trihydroxy-20-oxo-5α-pregnan-18-al

F

3β,11β,21-trihydroxy-20-oxo-5β-pregnan-18-al

3β,11β,21-trihydroxy-20-oxo-5β-pregnan-18-al

G

polar metabolites

polar metabolites

Conditions
ConditionsYield
With Tris-HCl buffer; adult male Sprague-Dawley rat liver microsomes; NADPH; magnesium chloride at 37℃; for 0.0833333h; Kinetics; <3H>labeled, Km, Vmax;
aldosterone
52-39-1

aldosterone

C22H31(2)H2NO5

C22H31(2)H2NO5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tris-HCl buffer, NADH / 7 h / Ambient temperature; 3α,20β-hydroxysteroid dehydrogenase
2: pyridine / Ambient temperature
View Scheme
aldosterone
52-39-1

aldosterone

C23H34(2)H2N2O5

C23H34(2)H2N2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tris-HCl buffer, NADH / 7 h / Ambient temperature; 3α,20β-hydroxysteroid dehydrogenase
2: pyridine / Ambient temperature
View Scheme
aldosterone
52-39-1

aldosterone

3β,11β-dihydroxy-18-nor-5α-androstane-13β,17β-dicarboxylic acid-13=>11-lactone
112442-39-4

3β,11β-dihydroxy-18-nor-5α-androstane-13β,17β-dicarboxylic acid-13=>11-lactone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; aqueous sodium periodate solution
2: platinum; acetic acid / Erhitzen des Reaktionsprodukts mit Hydrazin-hydrat und Natriumaethylat in Aethanol auf 150grad
View Scheme
aldosterone
52-39-1

aldosterone

3β,11β-dihydroxy-18-nor-5α-androstane-13β,17β-dicarboxylic acid-13=>11-lactone-17-methyl ester
102443-94-7

3β,11β-dihydroxy-18-nor-5α-androstane-13β,17β-dicarboxylic acid-13=>11-lactone-17-methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol; aqueous sodium periodate solution
2: platinum; acetic acid; pyridine / Hydrogenation.Reaktion ueber zwei Stufen
3: hydrazine hydrate; sodium ethylate; ethanol / 150 °C / Behandeln des Reaktionsprodukts mit Diazomethan in Aether
View Scheme
aldosterone
52-39-1

aldosterone

(18Ξ)-3β-acetoxy-11β,18-epoxy-18-hydroxy-5α-androstane-17β-carboxylic acid-lactone
124222-50-0

(18Ξ)-3β-acetoxy-11β,18-epoxy-18-hydroxy-5α-androstane-17β-carboxylic acid-lactone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; aqueous sodium periodate solution
2: platinum; acetic acid; pyridine / Hydrogenation.Reaktion ueber zwei Stufen
View Scheme
aldosterone
52-39-1

aldosterone

C34H51NO8

C34H51NO8

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 40 °C
3.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 - 40 °C
3.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
View Scheme
aldosterone
52-39-1

aldosterone

C25H35NO6

C25H35NO6

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 40 °C
3.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 - 40 °C
3.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C
View Scheme
aldosterone
52-39-1

aldosterone

C29H43NO6

C29H43NO6

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 40 °C
View Scheme
Multi-step reaction with 2 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 - 40 °C
View Scheme
aldosterone
52-39-1

aldosterone

C26H37NO6

C26H37NO6

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 - 40 °C
3.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C
5.1: thionyl chloride / 0 - 70 °C
View Scheme
aldosterone
52-39-1

aldosterone

C25H37NO5

C25H37NO5

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 - 40 °C
3.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C
5.1: thionyl chloride / 0 - 70 °C
6.1: sodium tetrahydroborate / methanol / 0 - 20 °C
View Scheme
aldosterone
52-39-1

aldosterone

C29H38N2O6

C29H38N2O6

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dmap; methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C
1.2: 2 h / 60 °C
2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3 h / 20 - 40 °C
3.1: triethylamine / dichloromethane / 1 h / 10 - 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C
5.1: thionyl chloride / 0 - 70 °C
6.1: sodium tetrahydroborate / methanol / 0 - 20 °C
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 70 °C / Inert atmosphere
View Scheme

52-39-1Relevant articles and documents

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Substrate solubility in steroid biotransformation is critical for improving the biotransformation of hydrophobic substrates. The present investigation describes the effect of some organic solvents, polyoxyethylene sorbitan monooleate (Tween 80; surfactant

Pharmaceutical composition and process of treatment

-

, (2008/06/13)

A process for alleviating proliferative skin diseases such as psoriasis, atopic dermatitis, etc. comprising administering to humans, or domesticated animals, topically and/or systemically a composition comprising a pharmaceutical carrier and at least one active compound selected from the groups, substituted alkyl zanthines, tricyclic antidepressants, organic nitrates, antihypertensives, anti-asthma agents and central nervous system depressants and combinations of certain compounds from specifically named groups of compounds.

The biosynthetic preparation of [16-3H]aldosterone and [16-3H] corticosterone.

AYRES,PEARLMAN,TAIT,TAIT

, p. 230 - 236 (2007/11/09)

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