Basic information
- CAS
485-19-8- Standard SMILES
COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O- InChIKey
BHLYRWXGMIUIHG-HNNXBMFYSA-N- Molecular formula
- C19H23NO4
- Average molar mass
- 329.4 g/mol
- Monoisotopic mass
- 329.16270821
Overview
(S)-reticuline is the (S)-enantiomer of reticuline. It has a role as an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor. It is a conjugate base of a (S)-reticulinium(1+). It is an enantiomer of a (R)-reticuline.
Names & identifiers
- Preferred name
- Reticuline
- IUPAC
- (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
- English name
- (S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol
- Molecular formula
- C19H23NO4
- Molecular weight
- 329.39
Names & synonyms
Reticulined-ReticulineS-(+)-ReticulineReticulinX35Z551WT4(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol(S)-1,2,3,4-Tetrahydro-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methylisoquinolin-7-ol(R,S)-ReticulineCHEBI:26533Reticular FiberReticulin FiberReticular Fibers
Show more names
(S)-ReticulineReticuline (>90% ee)(S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol(1S)-1-[(3-hydroxy-4-methoxy-phenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol2-Methoxy-5-[[(1S)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline]-1-ylmethyl]phenol[1S,(+)]-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-, (1S)-
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 62.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 407
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 125 · 125-126°C
- Boiling point
- 648.96 °C · 648.96°C (rough estimate)
- Density
- 1.4371 · 1.4371 (rough estimate)
- refractive index
- 1.68 · 1.6800 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Soluble in DMSO
- pka
- 9.95 · 9.95±0.10(Predicted)
- form
- Solid
- color
- Off-white to yellow
- optical activity
- 88.318 · +88.318 (c 0.21, ethanol)
- InChI
- InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Other Safety InformationIMAP assessments - 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-, (S)-: Human health tier I assessment
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301+H311+H331-H315-H319
- Precautionary statements
- P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesReticulin can be used to improve production of morphinan alkaloids, as well as its anti-inflammatory properties. It can also be used to lead scaffolds as PDE5A inhibitors and antihypertensives.
UsesPrecursor of many aporphine and morphine-type alkaloids.
Upstream & downstream products
Upstream raw materials
Suppliers72 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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