Basic information
- CAS
27003-73-2- Standard SMILES
COc1cc(C[C@H]2CO[C@H](c3ccc(O)c(OC)c3)[C@H]2CO)ccc1O- InChIKey
MHXCIKYXNYCMHY-AUSJPIAWSA-N- Molecular formula
- C20H24O6
- Average molar mass
- 360.4 g/mol
- Monoisotopic mass
- 360.15728849
Overview
(+)-lariciresinol is a lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). It has a role as an antifungal agent and a plant metabolite. It is a primary alcohol, a lignan, a member of oxolanes, a member of phenols and an aromatic ether. It is an enantiomer of a (-)-lariciresinol.
Names & identifiers
- Preferred name
- (+)-Lariciresinol
- IUPAC
- 4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
- English name
- (+)-LARICIRESINOL
- Molecular formula
- C20H24O6
- Molecular weight
- 360.4
Names & synonyms
Lariciresinol(+)-Lariciresinol27003-73-2NSC-32924773XCE5OZB04-((2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methoxyphenolCHEBI:67246DTXSID303183623-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-vanillyl-3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2S,3R,4R)-4-[(2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl]-2-methoxyphenollarici-resinol
Show more names
LariciresilLarch resinolLariciresinol, 10 mM in DMSOinhibit,Inhibitor,Lariciresinol(2S)-2α-(3-Methoxy-4-hydroxyphenyl)-4β-(3-methoxy-4-hydroxybenzyl)tetrahydrofuran-3β-methanol2α-(4-Hydroxy-3-methoxyphenyl)-3β-(hydroxymethyl)-4β-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran
RefChem:40974DTXCID70269485CHEMBL518421NSC3292474-[[(3R,4R,5S)-4-(hydroxymethyl)-5-(3-methoxy-4-oxidanyl-phenyl)oxolan-3-yl]methyl]-2-methoxy-phenolLaricericinolLariciresinol, (+)-3-Furanmethanol,tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (2S,3R,4R)-
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 88.4 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 433
Physicochemical properties
- Melting point
- 167 · 167-168 °C
- Boiling point
- 568.4 · 568.4±50.0 °C(Predicted)
- Density
- 1.261 · 1.261±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Powder
- pka
- 9.91 · 9.91±0.35(Predicted)
- color
- White to off-white
- BRN
- 4560057 · 4560057
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChI
- InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
- InChIKey
- MHXCIKYXNYCMHY-AUSJPIAWSA-N
- SMILES
- O1C[C@H](CC2=CC=C(O)C(OC)=C2)[C@H](CO)[C@H]1C1=CC=C(O)C(OC)=C1
- LogP
- 1.64 · 1.640 (est)
Safety & regulation
GHS classification
GHS Classification
Warning
H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAquatic Acute 1 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- risk_code
- 50
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- hazard_code
- N
- safety_code
- 61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H400
- Hazard Classifications
- Aquatic Acute 1
- Precautionary statements
- P273-P391-P501
Chemistry & industry
Applications
Uses(+)-Lariciresinol is used in biological studies as an anti-tumor-initiating effects of phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis to evaluate the pharmacological activity.
Suppliers78 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]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
Aladdin Scientific[email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
Related reactions
2 records
Compound notes
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