2451-01-6

Basic information

• Product Name: TERPIN MONOHYDRATE
• Synonyms: Terpin Hydrate (750 mg);cis-4-Hydroxy-α,α,4-trimethylcyclohexanemethanol monohydrate;cis-Terpin monohydrate;Terpin P-MENTHANE-1,8-DIOL, MONOHYDRATE;P-MENTHANE-1,8-DIOL, HYDRATE;TERPIN HYDRATE;TERPIN HYDRATE, MONOHYDRATE
• CAS NO: 2451-01-6
• Molecular Formula: C₁₀H₂₀O₂*H₂O
• Molecular Weight: 190.28
• EINECS: 209-279-5
• Product Categories: Biochemistry;Monocyclic Monoterpenes;Terpenes
• Mol File: 2451-01-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 116-117°C
• Boiling Point: bp 258°
• Flash Point: 156.8 °C
• Appearance: colorless ,lustrous crystal or white powder
• Density: 1.019g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: 3.42g/L(25 oC)
• Merck: 14,9169
• CAS DataBase Reference: TERPIN MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERPIN MONOHYDRATE(2451-01-6)
• EPA Substance Registry System: TERPIN MONOHYDRATE(2451-01-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 3265 8 / PGII
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2451-01-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless, lustrous, rhombic, crystalline prisms or white powder; slight characteristic odor; slightly bitter taste. Efflorescent. Soluble in alcohol and ether; slightly soluble in water. Combustible.

Uses

Different sources of media describe the Uses of 2451-01-6 differently. You can refer to the following data:
1. Used in screening of essential oil from Artemisia scoparia leaves for free radical scavenging activity
2. Pharmaceuticals, source of terpineol, medicine (expectorant).

Purification Methods

Crystallise terpin from H2O or EtOH. The anhydrous cis-isomer distils at 258o/760mm but hydrates on exposure to moist air. Anhydrous terpin is also obtained by recrystallisation from absolute EtOH. [Sword J Chem Soc 127 1632 1925, Lombard & Ambrose Bull Soc Chim Fr 230 1961, Beilstein 5 IV 435.]

InChI:InChI=1/C10H20O2/c1-9(2,11)8-4-6-10(3,12)7-5-8/h8,11-12H,4-7H2,1-3H3/t8-,10+

Synthetic route

methyl magnesium iodide (917-64-6) + 4c-hydroxy-4t-methyl-cyclohexane-r-carboxylic acid methyl ester (85977-96-4) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

rac-α-pinene (80-56-8) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
With emulsifierene; sulfuric acid

ethanol (64-17-5) + nitric acid (7697-37-2) + limonene. (138-86-3) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
dl-limonene;

Beta-pinene (177698-19-0) + sulfuric acid (7664-93-9) + potassium sulfate → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
Kinetics; levorotatory form;

Beta-pinene (177698-19-0) + sulfuric acid (7664-93-9) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) + sulfate of lower-melting pinene hydrate

Conditions	Yield
at 15 - 20℃; levorotatory form;

sulfuric acid (7664-93-9) + (S)-(+)-linalool (126-90-9) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Nerol (106-25-2) + sulfuric acid (7664-93-9) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Geraniol (106-24-1) + sulfuric acid (7664-93-9) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

ethanol (64-17-5) + 1-Chloro-4-(1-chloro-1-methyl-ethyl)-1-methyl-cyclohexane (4497-96-5) + water (7732-18-5) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
'trans-form';

methanol (67-56-1) + Pinene (80-56-8, 177698-18-9) + nitric acid (7697-37-2) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
dl-pinene;

Pinene (80-56-8, 177698-18-9) + ethanol (64-17-5) + nitric acid (7697-37-2) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
dl-pinene;

Pinene (80-56-8, 177698-18-9) + alcoholic aqueous hydrochloric acid → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
dl-pinene;

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3) + H3PO4(85 percent ) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
at -5℃;

linalool (126-91-0) + sulfuric acid (7664-93-9) → Nerol (106-25-2) + Geraniol (106-24-1) + cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) + d-terpineol

Pinene (80-56-8, 177698-18-9) + diluted formic acid → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) + limonene. (138-86-3) + levorotatory α-terpinyl formate

Conditions	Yield
l-pinene;

hydrogenchloride (7647-01-0) + terpineol (98-55-5) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
dl-α-terpineol;

terpineol (98-55-5) + sulfuric acid (7664-93-9) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
dl-α-terpineol;
at 0℃; dl-α-terpineol;

sulfuric acid (7664-93-9) + trans-2,6,6-trimethylbicyclo(3.1.1)-heptan-2-ol (473-54-1) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
pinene hydrate;

sulfuric acid (7664-93-9) + beta-terpineol (138-87-4, 7299-40-3, 7299-41-4, 148552-65-2) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

α-terpinyl chloride (39864-10-3) + water (7732-18-5) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
d-limonene monohydrochloride;

terpineol (98-55-5) + hydrogen ferrocyanidoic acid → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6)

Conditions	Yield
Behandeln des Reaktionsprodukts mit Aether oder Sodaloesung; dl-α-terpineol;

sulfuric acid (7664-93-9) + beta-pinene (18172-67-3, 19902-08-0) → cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) + terpineol

Conditions	Yield
at 0℃;

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → 1,8-Cineole (470-82-6)

Conditions	Yield
With chloroacetone
bei Einwirkung von Saeuren;

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → Terpinolene (586-62-9)

Conditions	Yield
With phosphoric acid
With sulfuric acid

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5)

Conditions	Yield
With phosphoric acid at 150 - 160℃;
With sulfuric acid
Multi-step reaction with 2 steps 1: concentrated hydrobromic acid 2: alcoholic sulfuric acid View Scheme
Multi-step reaction with 2 steps 1: bei der Einw. von wasserabspaltenden Mitteln 2: diluted sulfuric acid View Scheme

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → β-terpineol (7299-41-4, 148552-65-2)

Conditions	Yield
Dehydratisierung;

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → Menthane (99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5)

Conditions	Yield
With phosphorus; hydrogen iodide at 210℃;

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → 4-methylisopropylbenzene (99-87-6)

Conditions	Yield
With Japanese Fuller's earth
With bromine

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → 1-Chloro-4-(1-chloro-1-methyl-ethyl)-1-methyl-cyclohexane (4497-96-5)

Conditions	Yield
With hydrogenchloride 'trans-form';
With hydrogenchloride; phosphorus trichloride 'trans-form';
Multi-step reaction with 2 steps 1: bei der Einw. von wasserabspaltenden Mitteln 2: diethyl ether; hydrogen chloride View Scheme

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → 1,8-dibromo-p-menthane (1127-33-9)

Conditions	Yield
With hydrogen bromide trans-form;
With hydrogen bromide cis-form;

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → terpineol (98-55-5)

Conditions	Yield
With sulfuric acid dl-α-terpineol;
With oxalic acid dl-α-terpineol;
With sulfuric acid; benzene

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → terpineol (98-55-5) + beta-terpineol (138-87-4, 7299-40-3, 7299-41-4, 148552-65-2)

Conditions	Yield
bei der Einw. von wasserabspaltenden Mitteln; dl-α-terpineol;
With oxalic acid dl-α-terpineol;

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → terpineol (98-55-5) + limonene. (138-86-3)

Conditions	Yield
With Japanese acid earth at 200℃; bei der Destillation; dl-α-terpineol;

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → γ-terpineol (586-81-2)

Conditions	Yield
With sulfuric acid

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → beta-terpineol (138-87-4, 7299-40-3, 7299-41-4, 148552-65-2)

Conditions	Yield
With sulfuric acid
bei der Einw. von wasserentziehenden Mitteln;

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → 1,8-diiodo-p-menthane

Conditions	Yield
With carbon disulfide; phosphorous triiodide
With hydrogen iodide
Multi-step reaction with 2 steps 1: bei der Einw. von wasserabspaltenden Mitteln 2: hydrogen iodide View Scheme

cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate (2451-01-6) → limonene. (138-86-3)

Conditions	Yield
With phosphoric acid at 200℃;
With potassium hydrogensulfate Abdestillieren des entstehenden Wassers;
With copper at 300℃;

Upstream product

• 917-64-6 methyl magnesium iodide 
• 85977-96-4 4c-hydroxy-4t-methyl-cyclohexane-r-carboxylic acid methyl ester 
• 64-17-5 ethanol 
• 7697-37-2 nitric acid 
• 138-86-3 limonene. 
• 177698-19-0 Beta-pinene 
• 7664-93-9 sulfuric acid 
• 126-91-0 linalool 
• 80-56-8 Pinene 
• 18172-67-3 beta-pinene 
• 98-55-5 terpineol 
• 39864-10-3 α-terpinyl chloride 
• 7732-18-5 water 
• 138-87-4 beta-terpineol 

Downstream Products

• 123-76-2 levulinic acid 
• 116-51-8 terpenylic acid 
• 4436-81-1 homoterpenylmethylketone 
• 109089-58-9 phenyl-carbamic acid p-menth-8-en-1-yl ester 
• 90113-41-0 4-hydroxy-4-methylcyclohexane-1-carboxylic acid 
• 85734-09-4 p-menthane-1,8,9-triol 
• 109089-58-9 1-phenylcarbamoyloxy-1r-methyl-4t-isopropenyl-cyclohexane 
• 5034-20-8 1-(4-hydroxy-4-methylcyclohexyl)ethan-1-one 
• 99977-24-9 1,8-dinitro-p-menthane 
• 4342-60-3 4-methylcyclohex-3-enecarboxylic acid 
• 80-53-5 terpin hydrate 
• 138-86-3 limonene. 
• 138-87-4 beta-terpineol 
• 586-81-2 γ-terpineol