Name: Mevastatin
SKU: 73573-88-3

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Basic Information

Molecular Structure:
CAS No.:	73573-88-3
Name:	Mevastatin
Article Data:	18

Formula:	C₂₃H₃₄O₅
Molecular Weight:	390.52
Synonyms:	Butanoicacid, 2-methyl-,(1S,7S,8S,8αR)-1,2,3,7,8,8α-hexahydro-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenylester, (2S)-;Butanoicacid, 2-methyl-,1,2,3,7,8,8α-hexahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenylester, [1S-[1α(R),7b,8b(2S,4S*),8ab]]-;Antibiotic ML 236B;CS 500;CS 500(antibiotic);Compactin;Compactin (Penicillium);L 637312;ML 236B;ML 236Blactone;NSC 281245;Statin I;
EINECS:	700-442-0
Density:	1.13 g/cm³
Melting Point:	151-153 °C
Boiling Point:	555 °C at 760 mmHg
Flash Point:	186.5 °C
Solubility:	DMSO: 20 mg/mL
Appearance:	off-white solid
Hazard Symbols:	T+
Risk Codes:	26/27/28
Safety:	22-24/25-45-36/37/39
PSA:	72.83000
LogP:	3.94950

Synthetic route

: 79814-60-1
(1S,2S,8S,8aR,3'R,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-3',5'-dihydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-1-naphthaleneheptanoate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1.08333h; Ambient temperature;	70%
With toluene-4-sulfonic acid In benzene	70%

: 116996-42-0, 117065-49-3
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With Celite; silver carbonate In toluene at 95℃; for 2h;	61%

: 84751-53-1
(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -23℃; for 5h;	31%
With boron tribromide In dichloromethane at -23℃; for 6h;	31%

: 108713-03-7
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With hydrogen fluoride In water; acetonitrile at 45℃; for 8h;	30%

: 87000-71-3
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With hydrogen fluoride In acetonitrile at 25℃; for 0.5h; Yield given;

: 116996-42-0, 117065-49-3
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R,6S)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With Celite; silver carbonate In toluene at 95℃; for 2h; Yield given;

: 67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4
3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

: 73573-88-3
mevastatin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 25℃; for 0.5h;

: 67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4
(R)-3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

A: 73573-88-3
mevastatin

B: 84173-31-9
3,5-bis-epi-compactin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 25℃; for 0.25h;	A 32 mg B 22 mg

: 67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4
methyl 3,5-dihydroxy-7-<(1'S,2'S,8'S,8a'S)-2'methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',3',7',8',8a'-hexahydro-1'-naphthyl>heptanoate

A: 73573-88-3
mevastatin

B: 84173-31-9
3,5-bis-epi-compactin

Conditions

Conditions	Yield
With pyridine hydrogenfluoride In acetonitrile at 0℃; for 6h;	A 15.6 mg B 15.4 mg

: 116996-36-2, 117065-47-1
(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-((1S,2S,8aR)-2-methyl-8-triethylsilanyloxy-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-[1,3]dioxane

: 73573-88-3
mevastatin

Conditions

Yield

Multi-step reaction with 8 steps
1: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
2: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
3: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
4: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
5: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
6: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
7: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Multi-step reaction with 8 steps
1: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
2: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
3: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
4: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
5: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
6: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
7: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme

Total:142 Page 1 of 4 1 2 3 4 Next>>

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History

MEVASTATIN(73573-88-3) was the first compound isolated in the 70s during research into HMG-CoA reductase inhibitors produced by a mould Penicillium citrinum

Specification

The IUPAC name of Mevastatin is [(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate. With the CAS registry number 73573-88-3, it is also named as Compactin. The product's categories are Active Pharmaceutical Ingredients; Various Metabolites and Impurities; Metabolites; Pharmaceuticals; HMG-CoA Reductase, and the other registry numbers are 58948-09-7; 60478-65-1. Besides, it is off-white solid, which should be stored in sealed containers in a cool, dry place at 2-8 °C away from oxidizing agents. In addition, its molecular formula is C₂₃H₃₄O₅ and molecular weight is 390.52.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.57; (4)ACD/LogD (pH 7.4): 3.57; (5)ACD/BCF (pH 5.5): 306.24; (6)ACD/BCF (pH 7.4): 306.24; (7)ACD/KOC (pH 5.5): 2094.71; (8)ACD/KOC (pH 7.4): 2094.71; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.535; (13)Molar Refractivity: 107.1 cm³; (14)Molar Volume: 343.8 cm³; (15)Surface Tension: 44.5 dyne/cm; (16)Density: 1.13 g/cm³; (17)Flash Point: 186.5 °C; (18)Melting Point: 151-153 °C; (19)Solubility: DMSO: 20 mg/mL; (20)Enthalpy of Vaporization: 96.1 kJ/mol; (21)Boiling Point: 555 °C at 760 mmHg; (22)Vapour Pressure: 1.25E-14 mmHg at 25 °C.

Preparation of Mevastatin: this chemical can be prepared by 2-Methyl-butyric acid 8-[2-(4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester.

This reaction needs Ag₂CO₃/Celite and Toluene at temperature of 95 °C. The reaction time is 2 hours. The yield is 61 %.

Uses of Mevastatin: this chemical is a hypolipidemic agent. It is also used as a HMG-CoA reductase inhibitor. Similarly, it can be used to produce Desmethylmonacolin J.

This reaction needs aq. LiOH by heating for 1 day. The yield is 75 %.

When you are using this chemical, please be cautious about it as the following: it is very toxic by inhalation, in contact with skin and if swallowed. Please do not breathe dust. And you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin and eyes. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(O[C@@H]1[C@H]3C(=C/CC1)\C=C/[C@@H]([C@@H]3CC[C@H]2OC(=O)C[C@H](O)C2)C)[C@@H](C)CC
(2)InChI: InChI=1/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
(3)InChIKey: AJLFOPYRIVGYMJ-INTXDZFKBX

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	oral	> 2gm/kg (2000mg/kg)		Journal of Antibiotics. Vol. 29, Pg. 1346, 1976.
mouse	LD50	intraperitoneal	500mg/kg (500mg/kg)		Journal of Antibiotics. Vol. 29, Pg. 1346, 1976.