Beclomethasone dipropionate

Iupac Name：[2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate

CAS No.: 5534-09-8

Molecular Weight：521.04218

Modify Date.: 2022-11-29 05:51

Introduction: Beclomethasonedipropionate (Beclovent, Beconase, Vanceril, Vancenase)(BDP) is rapidly converted in the lungs to beclomethasone17-monopropionate (17-BMP), the metabolite that providesthe bulk of the anti-inflammatory activity. The monopropionatealso has higher affinity for the GR than either thedipropionate or beclomethasone. The portion of BDP that isswallowed is rapidly hydrolyzed to 17-BMP, 21-BMP(which arises by a transesterification reaction from 17-BMP), and beclomethasone itself. Beclomethasone hasmuch less GC activity than the monopropionate. View more+

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1. Names and Identifiers

1.1 Name: Beclomethasone dipropionate
1.2 Synonyms: (11b,16b)-9-Chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-pregna-1,4-diene-3,20-dione (11b,16b)-9-chloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-diene-17,21-diyl dipropanoate (11Β,16Β)-9-Chloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-diene-17,21-diyl dipropanoate (8S,9R,10S,11S,13S,14S,16S,17R)-9-Chlor-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[(propanoyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-ylpropanoat (8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[(propanoyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propanoate 9-Chloro-11b-hydroxy-16b-methylpregna-1,4-diene-3,20-dione 17,21-Dipropionate 9-chloro-16-beta-methyl-11-beta,17,21-trihydroxy-pregna-1-4-diene-20-dione 9-Chloro-16-Β-methyl-11-Β,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-Dipropionate Anceron Andion beclacin becloforte Beclometasone dipropionate beclometasone17,21-dipropionate Beclomethasone dipropionate (USP) becloval beclovent Becodisks Beconasol becotide benconase EINECS 226-886-0 MFCD00135613 pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11b,16b)- Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11Β,16Β)- propanoate de (8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-triméthyl-3-oxo-17-[(propanoyloxy)acétyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodécahydro-3H-cyclopenta[a]phénanthrén-17-yle Vancenase AQ Viarex

1.3 CAS No.: 5534-09-8

1.4 CID: 21700

1.5 EINECS(EC#): 226-886-0

1.6 Molecular Formula: C28H37ClO7 (isomer)

1.7 Inchi: InChI=1S/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1

1.8 InChkey: KUVIULQEHSCUHY-XYWKZLDCSA-N

1.9 Canonical Smiles: CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)Cl)O)C)C)OC(=O)CC

1.10 Isomers Smiles: CCC(=O)OCC(=O)[C@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)Cl)O)C)C)OC(=O)CC

2. Properties

2.1 Density: 1.26

2.1 Melting point: 210 oC

2.1 Boiling point: 630.5 °C at 760 mmHg

2.1 Refractive index: 1.564

2.1 Flash Point: 335.1 °C

2.1 Precise Quality: 520.22300

2.1 PSA: 106.97000

2.1 logP: 4.08680

2.1 Λmax: 238nm(EtOH)(lit.)

2.2 Appearance: White crystalline powder

2.3 Chemical Properties: Light Yellow Solid

2.4 pKa: 13.02±0.70(Predicted)

2.5 Water Solubility: 2.08e-03 g/L

2.6 StorageTemp: Sealed in dry,2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A steroid ester comprising beclomethasone having propionyl groups at the 17- and 21-positions.

3.2 General Description: Beclomethasonedipropionate (Beclovent, Beconase, Vanceril, Vancenase)(BDP) is rapidly converted in the lungs to beclomethasone17-monopropionate (17-BMP), the metabolite that providesthe bulk of the anti-inflammatory activity. The monopropionatealso has higher affinity for the GR than either thedipropionate or beclomethasone. The portion of BDP that isswallowed is rapidly hydrolyzed to 17-BMP, 21-BMP(which arises by a transesterification reaction from 17-BMP), and beclomethasone itself. Beclomethasone hasmuch less GC activity than the monopropionate.

3.3 Usage: Antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical)

4. Safety and Handling

4.1 Symbol: GHS08

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: R60;R61

4.1 Safety Statements: S53;S36/37/39;S45

4.1 Hazard Declaration: H360

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P201-P308 + P313

4.1 WGK Germany: 3

4.1 RTECS: TU3805000

4.1 Safety: Hazard Codes:T,Xn
Risk Statements:60-61-36/37/38-20/21/22
60:May impair fertility
61:May cause harm to the unborn child
36/37/38:Irritating to eyes, respiratory system and skin
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:53-36/37/39-45-36-26
53:Avoid exposure - obtain special instruction before use
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:3
HS Code:29372100

4.2 Specification

The Beclometasone dipropionate, with the cas regsister number 5534-09-8 , has the IUPAC name of [9-Chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate. Besides, its product categories are various, including active pharmaceutical ingredients; intermediates & fine chemicals; pharmaceuticals; steroids; intracellular receptor. When store it, you should keep it at 2-8°C.

The characteristics of this chemical are as follows: (1)ACD/LogP: 4.59; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 4.59; (4)ACD/LogD (pH 7.4): 4.59; (5)ACD/BCF (pH 5.5): 1808.81; (6)ACD/BCF (pH 7.4): 1808.81; (7)ACD/KOC (pH 5.5): 7468.6; (8)ACD/KOC (pH 7.4): 7468.58; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 95.97; (13)Index of Refraction: 1.563; (14)Molar Refractivity: 133.38 cm³; (15)Molar Volume: 410.2 cm³; (16)Polarizability: 52.87×10^-24cm³; (17)Surface Tension: 51.5 dyne/cm; (18)Density: 1.26 g/cm³; (19)Flash Point: 335.1 °C; (20)Enthalpy of Vaporization: 106.88 kJ/mol; (21)Boiling Point: 630.5 °C at 760 mmHg; (22)Vapour Pressure: 1.51E-18 mmHg at 25°C; (23)Exact Mass: 520.222781; (24)MonoIsotopic Mass: 520.222781; (25)Topological Polar Surface Area: 107; (26)Heavy Atom Count: 36; (27)Complexity: 1050.

While dealing with this chemical, you should be very cautious. This is irritant to eyes, respiratory system and skin, and if by inhalation, in contact with skin and if swallowed, it will be very harmful. Besides, for being a kind of toxic chemical, it may at low levels cause damage to health. Then it may cause harm to the unborn child and may cause impair fertility to women. Therefore, people should be very cautious. Wear suitable protective clothing, gloves and eye/face protection, and avoid exposure - obtain special instructions before use. If in case of accident or if you feel unwell seek medical advice immediately (show the label where possible); Or in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

In addition, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)Cl)O)C)C)OC(=O)CC
(2)InChI: InChI=1S/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-
19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3?
(3)InChIKey: KUVIULQEHSCUHY-UHFFFAOYSA-N

Below are the toxicity information of this chemical:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	> 5gm/kg (5000mg/kg)	?	Drugs in Japan Vol. 6, Pg. 746, 1982.
mouse	LD50	subcutaneous	> 5gm/kg (5000mg/kg)	?	Drugs in Japan Vol. 6, Pg. 746, 1982.
mouse	LDLo	intraperitoneal	2gm/kg (2000mg/kg)	?	Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1037, 1971.
rabbit	LD	subcutaneous	> 750mg/kg (750mg/kg)	LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Yamaguchi Igaku. Yamaguchi Medicine. Vol. 19, Pg. 65, 1970.
rat	LC50	inhalation	> 51600ug/m3/2 (51.6mg/m3)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 2, Pg. 97, 1976.
rat	LD50	intraperitoneal	> 3gm/kg (3000mg/kg)	?	Oyo Yakuri. Pharmacometrics. Vol. 12, Pg. 863, 1976.
rat	LD50	oral	> 3750mg/kg (3750mg/kg)	?	Oyo Yakuri. Pharmacometrics. Vol. 12, Pg. 863, 1976.
rat	LD50	subcutaneous	> 1500mg/kg (1500mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Oyo Yakuri. Pharmacometrics. Vol. 12, Pg. 863, 1976.

View all

4.3 Toxicity: Oral-rat LD50: >3750 mg/kg; Oral-Mouse LD50: >5000 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

Specific target organ toxicity \u2013 repeated exposure, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H360 May damage fertility or the unborn child H373 May cause damage to organs through prolonged or repeated exposure
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention. P314 Get medical advice/attention if you feel unwell.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Other Information

6.0 Merck: 14,1019

6.1 Chemical Properties: Light Yellow Solid

6.2 Originator: Propaderm,Kyowa Hakko,Japan,1972

6.3 Uses: Antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical)

6.4 Uses: antiasthmatic, topical antiinflammatory

6.5 Uses: Anti-arrhythmia Agent, corticosteroids

6.6 Definition: ChEBI: A steroid ester comprising beclomethasone having propionyl groups at the 17- and 21-positions.

6.7 Manufacturing Process: 6 grams of 6β-methyl-1,4-pregnadiene-11β,17α,21-triol-3,20-dione-21-acetate is dissolved in a mixture of 35 ml of dimethylformamide and 6 ml of pyridine. To the resulting solution is added 2.5 ml of methanesulfonyl chloride and the reaction mixture maintained at 80°-85°C for about 1 hour. The resulting red solution is cooled in an ice bath and treated successively with 55 ml of methanol, 240 ml of 5% aqueous sodium bicarbonate and finally with 360 ml of water. The resulting reaction mixture is then allowed to stand at room temperature overnight after which the precipitated product is removed by filtration, washed repeatedly with water and dried to a constant weight in air at about 50°C to produce 6β-methyl-1,4,9(11)-pregnadiene-11α,21-diol-3,20- dione-21-acetate.
Hydrolysis of the acetate ester with alkali, e.g., sodium methoxide in methanol, affords the free alcohol, 16β-methyl-1,4,9(11)-pregnadiene-17α,21- diol-3,20-dione. To a suspension of 3 grams of 6β-methyl-1,4,9(11)- pregnadiene-17α,21-diol-3,20-dione-21-acetate 40 ml of acetone is added at 0°C with stirring 2 grams of N-chlorosuccinimide and then 7 ml of a perchloric acid solution prepared by dissolving 0.548 ml of 70% perchloric acid in 33 ml of water. The resulting reaction mixture is stirred at 0° for about 4 hours 45 minutes.
The excess of N-chlorosuccinimide is destroyed by the addition of about 15 drops of allyl alcohol and 180 ml of water is then added with stirring. This mixture is held at 0°C for about one hour. The precipitated 16β-methyl-1,4- pregnadiene-9α-chloro-11β,17α,21-triol-3,20-dione-21-acetate is recovered filtration. A solution of 250 mg of the chlorohydrin in 5 ml of 0.25N perchloric acid in methanol is stirred for about 18 hours at room temperature to produce 16β-methyl-9α-chloro-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione which is recovered by adding water to the reaction mixture and allowing the product to crystallize. Propionic anhydride is then used to convert this material to the dipropionate.

6.8 Brand name: Beclovent (GlaxoSmithKline); Beconase (GlaxoSmithKline); Qvar (3M Pharmaceuticals); Vanceril (Schering).

6.9 Therapeutic Function: Topical antiinflammatory, Glucocorticoid

6.10 Biological Functions: Beclomethasone dipropionate is used primarily as an inhalation aerosol therapy for asthma and rhinitis. A breakthrough in the discovery of new inhalation corticosteroids with reduced risks from systemic absorption was that the 17α-monopropionate ester of beclomethasone (17-BMP) was more active than BDP and 21-monopropionate (21-BMP) esters. Thus, BDP is a pro-drug that is rapidly metabolized by esterases in the lung and other tissues to its more active metabolite, 17-BMP, which has 30 times greater affinity for the GR than BDP and approximately 14 times dexamethasone (Table 33.5).

6.11 General Description: Beclomethasonedipropionate (Beclovent, Beconase, Vanceril, Vancenase)(BDP) is rapidly converted in the lungs to beclomethasone17-monopropionate (17-BMP), the metabolite that providesthe bulk of the anti-inflammatory activity. The monopropionatealso has higher affinity for the GR than either thedipropionate or beclomethasone. The portion of BDP that isswallowed is rapidly hydrolyzed to 17-BMP, 21-BMP(which arises by a transesterification reaction from 17-BMP), and beclomethasone itself. Beclomethasone hasmuch less GC activity than the monopropionate.

6.12 General Description: Beclomethasonedipropionate, 9-chloro-11β-hydroxy-16β-methyl-17,21-bis-(1-oxopropoxy)-pregna-1,4-diene-3,20-dione (Beconase,QVAR), is used in nasal sprays and aerosol formulations totreat allergic rhinitis and asthma.

6.13 Clinical Use: Beclomethasone dipropionate is a lipophilic prodrug that, when inhaled, shows a systemic bioavailability of approximately 20% of the administered dose. The 16β-methyl group decreases mineralocorticoid activity, and the 9α-chloro group increases both the glucocorticoid and mineralocorticoid activity, resulting in potent anti-inflammatory activity with little or no salt-retaining effects.

6.14 Side effects: The main adverse effects are headache, sinusitis, and pain. Beclomethasone dipropionate is metabolized to the more active 17α-monopropionate derivative during absorption from the lungs and then further metabolized to the free alcohol in the liver.

6.15 Metabolism: The dipropionate also is metabolized to the inactive 21-monopropionate in the liver. Beclomethasone dipropionate and its metabolites are mainly excreted in the feces, with less than 10% excreted in the urine.

6.16 Storage features: Treasury is ventilated, low temperature and dry; stored separately from food materials

6.17 Mesh: Drugs that are used to treat asthma. (See all compounds classified as Anti-Asthmatic Agents.)|A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)|Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

6.18 Absorption: Following oral inhalation of 320 mcg of beclomethasone dipropionate (BDP), the Cmax was 88 pg/mL and it was reached after 0.5 at post-administration. The mean Cmax of the major and most active metabolite, beclomethasone-17-monopropionate (17-BMP), was 1419 pg/mL at 0.7 hour post-dosing. In another pharmacokinetic study, the AUC of BDP and 17-BMP were 6660 and 6185 pgxh/mL, respectively. The Cmax was 35356 pg/mL for BDP and 2633 pg/mL for 17-BMP, and and the median time to reach these concentrations (Tmax) was 0.2 hours. In the same study, the AUC of 17-BMP following oral and intranasal administration were 10158 and 3660 pgxh/mL, respectively. The Cmax of 17-BMP following oral and intranasal administration were 703 and 310 pg/mL, respectively, and the Tmax was 4 hours. The total bioavailability of 17-BMP following oral and intranasal administration were 41% and 44%, respectively.|Regardless of the route of administration, beclomethasone dipropionate and its metabolites are predominantly excreted in the feces, with less than 10% of the drug and its metabolites being excreted in the urine.|Following intravenous administration, the steady-state volume of distribution was 20 L for beclomethasone dipropionate and 424 L for the active metabolite, beclomethasone-17-monopropionate.|Following intravenous administration, the clearance of beclomethasone dipropionate and 17-BMP were 150 L/h and 120 L/h, respectively.

6.19 Metabolism: During absorption, beclomethasone dipropionate is undergoes rapid and extensive hydrolysis mediated by esterases CYP3A to form beclomethasone-17-monopropionate (17-BMP), beclomethasone-21-monopropionate (21-BMP), and beclomethasone (BOH). 17-BMP is the major active metabolite with the most potent anti-inflammatory activity. About 95% of the total beclomethasone dipropionate administered via oral inhalation undergoes presystemic conversion to form 17-BMP in the lung.

6.20 Biological Half Life: Following intravenous administration, the half life of beclomethasone dipropionate was 0.5 hours while the half life of the active metabolite 17-BMP was 2.7 hours. Following oral and intranasal administration, the half life of 17-BMP was 8.8 and 5.7 hours, respectively.

6.21 Mesh Entry Terms: Aerobec

6.22 Use Classification: Human drugs -> Trimbow -> EMA Drug Category|Drugs for obstructive airway diseases -> Human pharmacotherapeutic group|Human drugs -> Trydonis -> EMA Drug Category|Human drugs -> Riarify (previously CHF 5993 Chiesi Farmaceutici S.p.A.) -> EMA Drug Category|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

7. Computational chemical data

Molecular Weight: 521.04218g/mol
Molecular Formula: C₂₈H₃₇ClO₇
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 520.2227812
Monoisotopic Mass: 520.2227812
Complexity: 1050
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 107
Heavy Atom Count: 36
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4OAAEAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGgIACAAAD1aggAICCAAABgCIAqDSCAIAAAAgAAAICAFAA0gAEBIBAQQCQAAFgAAIAYPIzPDPgAAAAAAAAADIAAZAADIQAYAADAAAAA==

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