3D Mol Similar

Lovastatin

: Iupac Name：[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate; CAS No.: 75330-75-5; Molecular Weight：404.547; Modify Date.: 2022-11-11 00:36; Introduction:
Lovastatin, with the chemical formula C24H36O5 and CAS registry number 75330-75-5, is a compound known for its cholesterol-lowering properties. This white, crystalline powder is derived from a natural product found in certain fungi. Lovastatin works by inhibiting an enzyme involved in cholesterol synthesis, thereby reducing the levels of LDL cholesterol in the blood. It is commonly prescribed as a medication to treat high cholesterol and prevent cardiovascular diseases. Lovastatin has been extensively studied and has shown efficacy in reducing the risk of heart attacks and strokes. However, it may also have some side effects, such as muscle pain and liver abnormalities. Overall, Lovastatin is an important pharmaceutical compound that plays a crucial role in managing cholesterol levels and promoting cardiovascular health.
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1. Names and Identifiers

: 1.1 Name; Lovastatin; 1.2 Synonyms; (+)-Mevinolin (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl (S)-2-Methylbutyrate (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl (2S)-2-methylbutanoate (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl-(2S)-2-methylbutanoat (2S)-2-Methylbutanoic acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester [1S-[1a(R*),3a,7b,8b(2S*,4S*),8ab]]-2-Methylbutanoic Acid1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl Ester 1,2,6,7,8,8a-Hexahydro-b,d-dihydroxy-2,6-dimethyl-8-(2-methyl-1-oxobutoxy)-1-naphthaleneheptanoic Acid d-Lactone 2b,6a-Dimethyl-8a-(2-methyl-1-oxobutoxy)mevinic Acid Lactone 6a-Methylcompactin Altocor Altoprev Antibiotic MB 530B Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)- MFCD00072164 msd803 Simvastatin Impurity 5; View all

1.3 CAS No.: 75330-75-5

1.4 CID: 53232

1.5 EINECS(EC#): 616-212-7

1.6 Molecular Formula: C24H36O5 (isomer)

1.7 Inchi: InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1

1.8 InChIkey: PCZOHLXUXFIOCF-BXMDZJJMSA-N

1.9 Canonical Smiles: CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C

1.10 Isomers Smiles: CC[C@H](C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)C

2. Properties

2.1 Density: 1.12

2.1 Melting point: 175℃

2.1 Boiling point: 559.2 oC at 760 mmHg

2.1 Refractive index: 320 ° (C=0.5, CH3CN)

2.1 Flash Point: 185.3 oC

2.1 Precise Quality: 404.25600

2.1 PSA: 72.83000

2.1 logP: 4.19550

2.1 Solubility: ethanol: soluble9.80-10.20mg/mL, clear, colorless to faintly yellow

2.2 AnalyticLaboratory Methods: Analyte: Lovastatin;; matrix: chemical identification; procedure: Infrared Absorption spectrophotometry with comparison to standards

2.3 Appearance: White solid

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: White Solid

2.6 Color/Form: Powder

2.7 Physical: Solid

2.8 pKa: 13.49±0.40(Predicted)

2.9 Water Solubility: 0.0004 mg/mL at 25 oC

2.10 Spectral Properties: Specific optical rotation @ 25 deg C for D (sodium) line: +323 deg (concentration 0.5 g in 100 ml acetonitrile)
UV max: 231, 238, 247 nm (A 1% 532, 621, 418)

2.11 Stability: Stable under recommended storage conditions.

2.12 StorageTemp: 2-8°C

2.13 Toxicity Summary: IDENTIFICATION AND USE: Lovastatin; is a white, non-hygroscopic crystalline powder. It is used for therapy as anticholesteremic agent, and Hydroxymethylglutaryl-CoA; (HMG-CoA;) reductase inhibitor. HUMAN EXPOSURE AND TOXICITY: Lovastatin;, like other inhibitors of HMG-CoA; reductase, occasionally causes myopathy manifested as muscle pain, tenderness or weakness with creatine; kinase above ten times the upper limit of normal. Myopathy sometimes takes the form of rhabdomyolysis with or without acute renal failure secondary to myoglobinuria, and rare fatalities have occurred. The risk of myopathy is increased by high levels of HMG-CoA; reductase inhibitory activity in plasma. There have been rare postmarketing reports of fatal and non-fatal hepatic failure in patients taking statins, including lovastatin;. Treatment of HL-60 cells with lovastatin; induced characteristic apoptosis in a dose-dependent manner. ANIMAL STUDIES: Lovastatin; produced optic nerve degeneration (Wallerian degeneration of retinogeniculate fibers) in clinically normal dogs in a dose-dependent fashion starting at 60 mg/kg/day. Vestibulocochlear Wallerian-like degeneration and retinal; ganglion cell chromatolysis were also seen in dogs treated for 14 weeks at 180 mg/kg/day. CNS vascular lesions, characterized by perivascular hemorrhage and edema, mononuclear cell infiltration of perivascular spaces, perivascular fibrin deposits and necrosis of small vessels, were seen in dogs treated with lovastatin; at a dose of 180 mg/kg/day. In mice given oral lovastatin; dosages of 100 or 500 mg/kg daily, an increase in the incidence of papilloma in the nonglandular mucosa of the stomach was observed. Since the glandular mucosa of the stomach in these rodents was not affected and the human stomach contains only glandular mucosa, the importance of this finding to humans is unclear. An increased incidence of hepatocellular carcinoma and adenoma was observed after 21 months in mice given oral lovastatin; 500 mg/kg daily. Drug-related testicular atrophy, decreased spermatogenesis, spermatocytic degeneration and giant cell formation were seen in dogs starting at 20 mg/kg/day. Direct dosing of neonatal rats by subcutaneous injection with 10 mg/kg/day of the open hydroxyacid form of lovastatin; resulted in delayed passive avoidance learning in female rats. Lovastatin; has been shown to produce skeletal malformations in offspring of pregnant mice and rats dosed during gestation at 80 mg/kg/day. Lovastatin; did not exhibit mutagenic potential in in vitro mammalian cell systems (rat or mouse hepatocytes, V-79 cell forward mutation study), in vitro (Chinese hamster ovary cell) or in vivo (mouse bone marrow) chromosomal aberration studies, or microbial (Ames test) systems with or without metabolic activation. There is some in vitro evidence, however, that inhibition of HMG-CoA; reductase can inhibit DNA synthesis during the S phase of the cell life cycle; this inhibition appears to result from depletion of mevalonic acid; and is independent of its conversion to cholesterol;.; View all

3. Use and Manufacturing

3.1 General Description: Lovastatin is a hexahydro naphthalene ester isolated from Aspergillus terreus broth. It is an inactive lactone only yielding activity upon hydrolysis after oral administration. It has a strong competitive inhibition on the HMG-CoA reductase in the liver. HMG-CoA reductase is rate-limiting enzyme for de novo cholesterol synthesis in vivo. The inhibition of the enzyme can block the conversion of HMG-CoA to methacrylic acid, causing significant reduction in cholesterol synthesis, and leading to increased expression of the liver LDL receptor which promotes the plasma LDL-C clearance. The reduction of cholesterol synthesis can also cause reduced synthesis of liver ApoB100, thus causing that reduction of VLDL synthesis. Clinical observations show that it has a good effect of lowering of plasma total cholesterol and LDLC on hypercholesterolemia caused by various kinds of reasons such as heterozygous familial hypercholesterolemia, polygenic hypercholesterolemia, and diabetes or kidney disease syndrome.Statins are the secondary metabolites of filamentous fungi. It is capable of selectively inhibiting the activity of HMG coenzyme A (HMG-CoA) reductase and blocking cholesterol biosynthesis, which is due to the similarity of its acid structure with HMG-CoA. These drugs currently used in humans (statin drugs, statins) are mainly either natural or synthetic statins. Natural statins include lovastatin, mevastatin, Pravastatin and simvastatin. Lovastatin is produced by the fermentation of Aspergillus terreus); mevastatin is produced through the fermentation of penicillium citrinum and further conversion by streptomyces carbophilus; Simvastatin is made by semi-synthesis (chemically modified side chains) through lovastatin. Synthetic statins include fluvastatin, cerivastatin and atorvastatin.; View all

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 116 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 116 companies. For more detailed information, please visit ECHA C&L website

Of the 13 notification(s) provided by 115 of 116 companies with hazard statement code(s):

H302 (23.48%): Harmful if swallowed [Warning Acute toxicity, oral]
H361 (73.04%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H372 (29.57%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501; View all

3.3 Methods of Manufacturing: Lovastatin; is the delta-lactone of mevinolinic acid; and is produced by fermentation of Aspergillus terreus. The drug has also been isolated as a fermentation metabolite of Monascus ruber.

3.4 Usage: It is used for treating heterozygous familial and non familial, secondary hyperlipidemia, namely diabetes and nephrotic syndrome secondary hypercholesterolemia. It can reduce the level of TC, LF, LDL-C, and increase the level of HDL-C, reduce the risk of myocardial infarction, unstable angina and the necessity for percutaneous transluminal coronary angioplasty (PTCA).

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S22;S24/25

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl lovastatin, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392). [

4.2 Packing Group: III

4.2 Octanol/Water Partition Coefficient: log Kow= 4.26

4.3 Hazard Class: 9

4.3 Hazard Declaration: H302

4.3 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.4 RIDADR: 3077

4.4 Caution Statement: P301 + P312 + P330

4.4 Formulations/Preparations: Oral Tablets, 10 mg, 20 mg, 40 mg: Lovastatin, Geneva, Teva; Mevacor, Merck
Lovalip, Mevacor, Mevinacor, Mevlor, Sivlor

4.5 WGK Germany: 3

4.5 RTECS: EK7907000

4.5 Safety: Hazard Codes of Lovastatin (CAS NO.75330-75-5):?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36/37/39-26?
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 3077
WGK Germany: 3
RTECS: EK7907000
HazardClass: 9
PackingGroup: III

4.6 Specification: ? Lovastatin ,?its cas register number is?75330-75-5. It also can be called?(1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate ; (S)-2-Methylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one ; 6-alpha-Methylcompactin ; 6alpha-Methylcompactin ; Cholestra ;
?Lipivas ; Lipofren ; Lovalip; Lovalord ; Lovasterol?; Mevinacor ; Mevinolin ; Mevlor ; Monacolin K ; Nergadan ; Paschol ; Rodatin .

4.7 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	17mg/kg/3W-I (17mg/kg)	BEHAVIORAL: WAKEFULNESS	Lancet. Vol. 343, Pg. 973, 1994.
human	TDLo	oral	8750ug/kg/14D (8.75mg/kg)	BEHAVIORAL: WAKEFULNESS BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)	Clinical Pharmacology and Therapeutics Vol. 50, Pg. 730, 1991.
man	TDLo	oral	240mg/kg/60W- (240mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS	Annals of Pharmacotherpy. Vol. 26, Pg. 190, 1992.
mouse	LD50	oral	> 1gm/kg (1000mg/kg)	?	Journal of Antibiotics. Vol. 32, Pg. 852, 1979.
women	TDLo	oral	285mg/kg/30W- (285mg/kg)	LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" LIVER: LIVER FUNCTION TESTS IMPAIRED SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Israel Journal of Medical Sciences. Vol. 28, Pg. 101, 1992.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1

Carcinogenicity, Category 2

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H317 May cause an allergic skin reaction H351 Suspected of causing cancer H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

75330-75-5Total: 25 Synthesis Route

79691-11-5

75330-75-5 406 Suppliers

Literatures:
Senanayake, Chris H.; Bill, Timothy J.; DiMichele, Lisa M.; Chen, Cheng Y.; Larsen, Robert D.; Verhoeven, Thomas R.; Reider, Paul J. Tetrahedron Letters, 1993 , vol. 34, # 38 p. 6021 - 6024
Yield: ~96%

75225-51-3 7 Suppliers

75330-75-5 406 Suppliers

Literatures:
LUPIN LIMITED Patent: WO2005/35515 A1, 2005 ; Location in patent: Page/Page column 17-18 ;
Yield: ~76%

85614-12-6

75330-75-5 406 Suppliers

Literatures:
Tetrahedron Letters, , vol. 34, # 38 p. 6021 - 6024
Yield: null

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7. Precursor and Product

precursor:

79902-31-1

117020-89-0

75225-51-3

116996-32-8

116996-31-7

153079-17-5

153079-18-6

153079-19-7

84131-91-9

27763-54-8

85614-12-6

117020-90-3

153079-20-0

153079-21-1

153079-22-2

116996-44-2

153079-24-4

116996-43-1

116996-46-4

116996-45-3

125975-03-3

117020-88-9

116996-48-6

116996-47-5

79691-11-5

View all

product :

75225-51-3

79902-31-1

151006-15-4

109273-98-5

132748-10-8

79902-63-9

75225-50-2

8. Other Information

8.0 Usage: Lovastatin is a cholesterol lowering drug and competitive inhibitor of HMG-CoA reductase, a rate limiting enzyme in cholesterol synthesis. Blocks the production of mevalonate, a critical compound in the production of cholesterol and isoprenoids. It increases cellular resistance to anticancer agents such as doxorubicin and induces apoptosis in myeloma cells. It causes cell cycle arrest in G1 and G2/M phases.

9. Computational chemical data

Molecular Weight: 404.547g/mol
Molecular Formula: C₂₄H₃₆O₅
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 404.25627424
Monoisotopic Mass: 404.25627424
Complexity: 666
Rotatable Bond Count: 7
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 72.8
Heavy Atom Count: 29
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: AAADcfB4OAAAAAAAAAAAAAAAAAAAAAAAAAAkQIAAAAAAAACAAAAAGgAACAAADRSggAICCAAABgCIAiDSCAAAAAAgAAAICAEAAAgIEBYAAQACQAAF4AAIgAOIzPDOgAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

What are the potential risks and side effects of Lovastatin? Jun 16 2024
Lovastatin is a novel fully synthetic hydroxymethylglutaryl-CoA reductase inhibitor and is one of the most effective lipid-lowering drugs currently available. Pharmacology and Toxicology Lovastatin c..
How can we effectively use Lovastatin? Oct 25 2023
Lovastatin is a commonly used medication, widely used to lower cholesterol and prevent cardiovascular diseases. So, how can we effectively use Lovastatin? This article will explore some methods and p..
How was Lovastatin Discovered and Synthesized? Jan 03 2023
In August 1979, shortly after Shoujiro Endo published his paper on monacolin K, researchers at Merck Pharmaceuticals announced that they had also isolated a compound called mevinolin from the culture ..
What are the adverse reactions caused by Lovastatin? Sep 28 2022
When using medication, many people are concerned about the effects and price of the drug, but they often overlook the adverse reactions. However, it is necessary to understand the adverse reactions of..

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12. Realated Product Infomation

79952-44-6 Epi Lovastatin

109273-98-5 Dehydro Lovastatin

149756-62-7 Lovastatin DiMer

1002346-03-3 LOVASTATIN-D9

1002345-93-8 Lovastatin-d3

75225-50-2 Lovastatin sodium salt

237073-64-2 LOVASTATIN AMMONIUM SALT

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