7564-64-9

Basic information

• Product Name: 3-METHYLPENTANE-1,3,5-TRIOL
• Synonyms: 3,5-Pentanetriol,3-methyl-1;5-pentanetriol,3-methyl-3;1,3,5-TRIHYDROXY-3-METHYLPENTANE;3-METHYLPENTANE-1,3,5-TRIOL;3-METHYL-1,3,5-PENTANETRIOL;Methylpentanetriol;3-METHYL-1 3 5-PENTANETRIOL TECH. 80%;3-METHYLPENTANE-1,3,5-TRIOL 80+%
• CAS NO: 7564-64-9
• Molecular Formula: C₆H₁₄O₃
• Molecular Weight: 134.17
• EINECS: 231-466-5
• Product Categories: Alcohols;Monomers;Polymer Science;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 7564-64-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 216 °C0.5 mm Hg(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 1.112 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.89E-05mmHg at 25°C
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: Room Temperature
• Solubility: Chloroform (Heated), DMSO (Soluble), Methanol (Slightly)
• PKA: 14.43±0.29(Predicted)
• CAS DataBase Reference: 3-METHYLPENTANE-1,3,5-TRIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLPENTANE-1,3,5-TRIOL(7564-64-9)
• EPA Substance Registry System: 3-METHYLPENTANE-1,3,5-TRIOL(7564-64-9)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 7564-64-9(Hazardous Substances Data)

Usage

Description

3-METHYLPENTANE-1,3,5-TRIOL, also known as 3-Methyl-1,3,5-pentanetriol, is an organic compound with the molecular formula C6H14O4. It is a triol, meaning it contains three hydroxyl (-OH) groups attached to a carbon chain. 3-METHYLPENTANE-1,3,5-TRIOL is known for its versatile chemical properties and is commonly used as a building block in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
3-METHYLPENTANE-1,3,5-TRIOL is used as an intermediate in the synthesis of Mevalonolactone (M339040) for its potential therapeutic applications. Mevalonolactone is a key compound in the mevalonate pathway, which plays a crucial role in the biosynthesis of cholesterol, dolichols, ubiquinones, and isoprenoid compounds. Its potential use in the development of drugs targeting this pathway makes 3-METHYLPENTANE-1,3,5-TRIOL an important precursor in the pharmaceutical industry.
Used in Vitamin and Isoprenoid Synthesis:
3-METHYLPENTANE-1,3,5-TRIOL is used as a starting material in the synthesis of vitamins and isoprenoids, such as steroids. Isoprenoids are a large and diverse class of natural organic compounds derived from isoprene units, and they play essential roles in various biological processes, including cell signaling, membrane integrity, and energy production. Vitamins, on the other hand, are essential nutrients required for various metabolic processes in the body. The ability of 3-METHYLPENTANE-1,3,5-TRIOL to be converted into these vital compounds highlights its importance in the chemical and pharmaceutical industries.

InChI:InChI=1/C6H14O3/c1-6(9,2-4-7)3-5-8/h7-9H,2-5H2,1H3

Synthetic route

3-Methyl-1,5-bis-(tetrahydro-pyran-2-yloxy)-pentan-3-ol → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 4h; Heating;	90%

dimethyl 3-hydroxy-3-methylglutarate (56652-39-2) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With boron trifluoride-tetrahydrofuran complex for 18h; Heating;	88%

meglutol (503-49-1) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h;	45%
Multi-step reaction with 2 steps 1: 91 percent / SOCl2 / 0 °C 2: 88 percent / BF3*THF / 18 h / Heating View Scheme

mevalonolactone (674-26-0) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Reflux;	2.1 g

1,1-diallylethanol (25201-40-5) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
(i) O3, CH2Cl2, (ii) LiAlH4, THF; Multistep reaction;
With ozone 1.) -50 deg C, 20-30 min; Yield given. Multistep reaction;

1,1-diallylethanol (25201-40-5) → (R/S)-3-methyl-5-hexene-1,3-diol (114580-75-5) + 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride; ozone Product distribution; 1.) CH2Cl2, -78 deg C, 7 min; 2.) THF, RT, 12 h; different ozonolysis temperature;
With lithium aluminium tetrahydride; ozone 1.) CH2Cl2, -78 deg C, 7 min; 2.) THF, RT, 12 h; Yield given. Multistep reaction. Yields of byproduct given;

4-(β-hydroxyethyl)-4-methyl-1,3-dioxane (2018-45-3) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With oxalic acid at 150℃; under 4484 Torr; for 2.5h;

[1,3]oxathiolane-2,2-diyl-bis-acetic acid diethyl ester (86447-05-4) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 2: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 3: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 4: 1) Mg / 1) ether, 2) 0 deg C, 15 min 5: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

2,2'-(1,3-oxathiolane-2,2-diyl)bisethanol (86447-06-5) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 2: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 3: 1) Mg / 1) ether, 2) 0 deg C, 15 min 4: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

2,2-bis[2-(tetrahydropyran-2-yloxy)ethyl]-1,3-oxathiolane (86447-07-6) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 2: 1) Mg / 1) ether, 2) 0 deg C, 15 min 3: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

1,5-bis(tetrahydropyran-2-yloxy)pentan-3-one (86447-08-7) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) Mg / 1) ether, 2) 0 deg C, 15 min 2: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

diethyl 1,3-acetonedicarboxylate (105-50-0) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: 92 percent / BF3*Et2O / CH2Cl2 / 6 h / Ambient temperature 2: 90 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 3: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 4: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 5: 1) Mg / 1) ether, 2) 0 deg C, 15 min 6: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

(R)-mevalonolactone (19115-49-2) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
In tetrahydrofuran

3-methyl-1,3,5-pentanetriol (7564-64-9) + benzaldehyde (100-52-7) → 1,3-O,O-benzylidene-3-methylpentane-1,3,5-triol (877308-88-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 60℃; for 18h;	100%
With toluene-4-sulfonic acid In toluene at 60℃; for 24h;	63%

3-methyl-1,3,5-pentanetriol (7564-64-9) → mevalonolactone (674-26-0)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 4h; Ambient temperature;	92%
With aluminum oxide; sodium bromite In dichloromethane for 1.5h; Ambient temperature;	85%
With peracetic acid; sodium bromide In ethyl acetate at 39.9℃; for 2h;	83%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate In acetonitrile at 22℃; for 6h;	83%

3-methyl-1,3,5-pentanetriol (7564-64-9) → meglutol (503-49-1)

Conditions	Yield
In acetic acid butyl ester; nitric acid	85%

3-methyl-1,3,5-pentanetriol (7564-64-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 1,5-bis-dimethoxytrityloxy-3-methyl-pentan-3-ol (1033113-30-2)

Conditions	Yield
With dmap In pyridine at 0 - 20℃;	78%

3-methyl-1,3,5-pentanetriol (7564-64-9) + p-toluenesulfonyl chloride (98-59-9) → 3-hydroxy-3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate)

Conditions	Yield
With dmap; triethylamine In acetonitrile at 0 - 20℃; for 5h; Inert atmosphere;	73%

3-methyl-1,3,5-pentanetriol (7564-64-9) + 2,2-dimethoxy-propane (77-76-9) → 1,3-O,O-isopropylidene-3-methylpentane-1,3,5-triol (154066-61-2)

Conditions	Yield
With camphor-10-sulfonic acid In acetone at 20℃; for 24h;	66%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80 - 90℃; for 3h;	42.5%

3-methyl-1,3,5-pentanetriol (7564-64-9) + epichlorohydrin (106-89-8) → 3-Methyl-1,5-bis-oxiranylmethoxy-pentan-3-ol

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 6h;	65%

3-methyl-1,3,5-pentanetriol (7564-64-9) + C6H11BO2 + sodium hydride (7646-69-7) → C10H16BO3(1-)*Na(1+)

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	63%

3-methyl-1,3,5-pentanetriol (7564-64-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-{[tert-butyl(dimethyl)silyl]oxy}-3-methylpentane-1,3-diol (861389-35-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	50%

3-methyl-1,3,5-pentanetriol (7564-64-9) + Trimethylhydroquinone (700-13-0) → 2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethanol (79907-48-5)

Conditions	Yield
With hydrogenchloride; zinc(II) chloride In 1,4-dioxane; toluene at 100℃; for 6h;	47%

pyridine (110-86-1) + Mn3O((CH3)3CCO2)6(pyridine)3 + 3-methyl-1,3,5-pentanetriol (7564-64-9) + tetramethyl ammoniumhydroxide (75-59-2) + acetonitrile (75-05-8) → (Me4N)2[MnIII13MnIV2O10(OH)2(3-methyl-1,3,5-pentanetriol(-3H))4(2-hydroxymethyl-3-methylbutane-1,3-diol(-3H))2((CH3)3CCO2)8(py)2]((CH3)3CCO2)2H*2py*2H2O

Conditions	Yield
for 1h;	25%

3-methyl-1,3,5-pentanetriol (7564-64-9) → 3-hydroxy-3-methylcadaverine (133213-14-6)

Conditions	Yield
With hydrogen azide; triphenylphosphine; 2,2'-azobis(isobutyronitrile) In tetrahydrofuran; benzene 1) RT, 1h, 2) 50 deg C, 3h; Yield given;

3-methyl-1,3,5-pentanetriol (7564-64-9) → (S)-mevalonolactone (19022-60-7) + (R)-mevalonolactone (19115-49-2)

Conditions	Yield
In water at 30℃; for 72h; Gluconobacter scleroideus IAM 1842; Yield given. Title compound not separated from byproducts;
In water at 30℃; Product distribution; different Gluconobacters and time of incubation;

3-methyl-1,3,5-pentanetriol (7564-64-9) → 1,3-O,O-isopropylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol (877308-89-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / camphorsulphonic acid / acetone / 24 h / 20 °C 2: 85 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 1,3-O,O-benzylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol (877308-90-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / p-toluenesulphonic acid monohydrate / toluene / 24 h / 60 °C 2: 90 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,3-diol

Conditions	Yield
Multi-step reaction with 3 steps 1: 63 percent / p-toluenesulphonic acid monohydrate / toluene / 24 h / 60 °C 2: 90 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C 3: 85 percent / ZnBr2 / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 66 percent / camphorsulphonic acid / acetone / 24 h / 20 °C 2: 85 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C 3: 86 percent / ZnBr2 / CH2Cl2 / 1 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-pentanal

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → ethyl (2E)-7-bromo-5-(methoxymethoxy)-5-methylhept-2-enoate

Conditions

Yield

Multi-step reaction with 6 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C 3: 60 percent / CH2Cl2 / -78 - 20 °C 4: 79 percent / diisopropylethylamine / CH2Cl2 / 0 - 20 °C 5: 81 percent / hydrogen fluoride; pyridine / tetrahydrofuran / 0 - 20 °C 6: 45 percent / carbon tetrabromide; triphenylphosphine / CH2Cl2 / 0 - 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → ethyl (2E)-7-hydroxy-5-(methoxymethoxy)-5-methylhept-2-enoate (861389-37-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C 3: 60 percent / CH2Cl2 / -78 - 20 °C 4: 79 percent / diisopropylethylamine / CH2Cl2 / 0 - 20 °C 5: 81 percent / hydrogen fluoride; pyridine / tetrahydrofuran / 0 - 20 °C View Scheme

Upstream product

• 56652-39-2 dimethyl 3-hydroxy-3-methylglutarate 
• 19115-49-2 (R)-mevalonolactone 
• 503-49-1 meglutol 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 86447-08-7 1,5-bis(tetrahydropyran-2-yloxy)pentan-3-one 
• 86447-07-6 2,2-bis[2-(tetrahydropyran-2-yloxy)ethyl]-1,3-oxathiolane 
• 86447-06-5 2,2'-(1,3-oxathiolane-2,2-diyl)bisethanol 
• 86447-05-4 [1,3]oxathiolane-2,2-diyl-bis-acetic acid diethyl ester 
• 2018-45-3 4-(β-hydroxyethyl)-4-methyl-1,3-dioxane 
• 25201-40-5 1,1-diallylethanol 
• 674-26-0 mevalonolactone 

Downstream Products

• 674-26-0 mevalonolactone 
• 117896-69-2 1-phenyl-4-hydroxypiperidine 
• 19125-34-9 1-phenylpiperidin-4-one 
• 871026-48-1 3,5-dihydroxy-3-methylpentyl benzoate 
• 503-49-1 meglutol 
• 154170-47-5 5-benzyloxy-3-methylpentane-1,3-diol 
• 154066-62-3 4-(2-Benzyloxy-ethyl)-2,2,4-trimethyl-[1,3]dioxane 
• 87137-49-3 methyl (RS)-5-benzyloxy-3-hydroxy-3-methylpentanoate 
• 101268-70-6 (RS)-5-benzyloxy-3-hydroxy-3-methylpentanoic acid 
• 60018-14-6 (S)-(-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol 
• 877308-90-2 1,3-O,O-benzylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol 
• 877308-89-9 1,3-O,O-isopropylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol 
• 877308-88-8 1,3-O,O-benzylidene-3-methylpentane-1,3,5-triol 

Relevant articles and documents

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