4-(2-Hydroxypropan-2-yl)-1-methylcyclohexan-1-ol--water (1/1)
Basic information
- CAS
2451-01-6- Standard SMILES
CC1(O)CCC(C(C)(C)O)CC1.O- InChIKey
JGKJMBOJWVAMIJ-UHFFFAOYSA-N- Molecular formula
- C10H22O3
- Average molar mass
- 190.28 g/mol
- Monoisotopic mass
- 190.15689456
Overview
Terpin hydrate is an expectorant, commonly used to loosen mucus and ease congestion in patients presenting with acute or chronic bronchitis, and related pulmonary conditions. It is derived from sources such as turpentine, oregano, thyme and eucalyptus. It was popular in the United States since the late nineteenth century, but was removed from marketed medications in the 1990s after FDA stated that "based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients". Elixirs of terpin hydrate are still available to patients as prescription medications to be prepared by specialty compounding pharmacies.
Names & identifiers
- Preferred name
- 4-(2-Hydroxypropan-2-yl)-1-methylcyclohexan-1-ol--water (1/1)
- IUPAC
- 4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol;hydrate
- English name
- TERPIN MONOHYDRATE
- Molecular formula
- C10H20O2.H2O
- Molecular weight
- 190.28
Names & synonyms
DTXSID00947401RefChem:1069832DTXCID1013756614-(2-Hydroxypropan-2-yl)-1-methylcyclohexan-1-ol--water (1/1)TERPIN HYDRATE2451-01-6Terpin monohydratep-Menthane-1,8-diol monohydrateTerpin (hydrate)Terpin cis-form hydratecis-Terpin hydrateTerpinol hydrate
Show more names
Terpin DIPENTENEGLYCOLcis-Form hydrateTerpineHydrateBpTerpin 1-hydrate(E)-terpin hydrate
terpinene hydrateMFCD00167312Cyclohexanemethanol, 4-hydroxy-alpha,alpha,4-trimethyl-, monohydraterel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrateSCHEMBL29867TERPIN HYDRATE [WHO-DD]cis-p-methane-1,8-diol monohydrateCis-p-menthane-1,8-diol monohydrate
Database identifiers
- CAS
2451-01-6- PubChem CID
- 17141
- DTXSID
DTXSID00947401- ChEMBL
CHEMBL2105614
Properties
Computed structural properties
- Topological polar surface area
- 41.5 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 155
Experimental & physicochemical properties
SolubilityPartially soluble in cold water
Physicochemical properties
- Melting point
- 116 · 116-117°C
- Boiling point
- 258 ° · bp 258°
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- 3.42 g/L · 3.42g/L(25 ºC)
- Merck
- 14 · 14,9169
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C10H20O2.H2O/c1-9(2,11)8-4-6-10(3,12)7-5-8;/h8,11-12H,4-7H2,1-3H3;1H2/t8-,10+;
- InChIKey
- JGKJMBOJWVAMIJ-OFAZAQPOSA-N
- SMILES
- O.CC(C)(O)[C@@H]1CC[C@](C)(O)CC1
- CAS DataBase Reference
- 2451 · 2451-01-6(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- tsca
- Yes
- ridadr
- UN 3265 8 / PGII
- hs_code
- 2906195000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 26-36/37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Pharmacodynamics
It acts to facilitate the removal of mucus from the respiratory tract. It prevents the exacerbation of excessive mucus production and secretion due to airway bacterial or viral infections, asthma or chronic bronchitis. Expectorants like terpin hydrate change mucus consistency and make coughing more productive.
Mechanism of Action
Terpin hydrate improves mucociliary function by working directly on the bronchial secretory cells in the lower respiratory tract to liquify and facilitate the elimination of bronchial secretionsas well as exerting a weak antiseptic effect on the pulmonary parenchyma. It is thought to increase the amount of fluid in the respiratory tract, which increases the flow and clearance of local irritants and as well as reducing the viscosity of mucus.
Applications
UsesUsed in screening of essential oil from Artemisia scoparia leaves for free radical scavenging activity
UsesPharmaceuticals, source of terpineol, medicine (expectorant).
Upstream & downstream products
Downstream products
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