40957-99-1

Usage

Uses

Used in Cosmetic and Personal Care Industry:
Medioresil is used as an emollient and skin conditioning agent for its moisturizing and softening effects on the skin. It is incorporated into lotions, creams, and sunscreens to provide a smooth and silky texture, enhancing the overall user experience.
Used in Skincare Formulations:
Medioresil is used as an ingredient in skincare products to improve spreadability and stability of the formulations. Its combination of medium chain triglycerides, silicone oil, and cetyl dimethicone contributes to the product's performance and longevity, making it a preferred choice for skincare manufacturers.

InChI:InChI=1/C21H24O7/c1-24-16-6-11(4-5-15(16)22)20-13-9-28-21(14(13)10-27-20)12-7-17(25-2)19(23)18(8-12)26-3/h4-8,13-14,20-23H,9-10H2,1-3H3/t13-,14-,20+,21+/m0/s1

Upstream product

• 458-35-5 coniferol 
• 20675-96-1 Syringenin 
• 6527-32-8 4-(benzyloxy)-3,5-dimethoxybenzaldehyde 
• 123195-63-1 4-benzyloxy-3-methoxybenzaldehyde-bis-phenylthioacetal 
• 1428768-22-2 2,6-dimethoxy-4-[(1S,3aR,4S,6aR)-4-(3-methoxy-4-{[(2Z)-2-methylbut-2-enoyl]oxy}phenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]phenyl (2Z)-2-methylbut-2-enoate 
• 97399-82-1 hedyotol-C 
• 67-64-1 acetone 
• 99633-12-2 medioresinol-4″-β-glucoside 
• 97400-05-0 hedyotol-C tetraacetate 

Downstream Products

• 136051-42-8 (7'R,8'S,8S)-5-methoxylariciresinol triacetate 
• 136051-41-7 (+)-5'-methoxylariciresinol 

Relevant academic research and scientific papers

Dirigent Proteins Guide Asymmetric Heterocoupling for the Synthesis of Complex Natural Product Analogues

Phenylpropanoids are a class of abundant building blocks found in plants and derived from phenylalanine and tyrosine. Phenylpropanoid polymerization leads to the second most abundant biopolymer lignin while stereo- and site-selective coupling generates an array of lignan natural products with potent biological activity, including the topoisomerase inhibitor and chemotherapeutic etoposide. A key step in etoposide biosynthesis involves a plant dirigent protein that promotes selective dimerization of coniferyl alcohol, a common phenylpropanoid, to form (+)-pinoresinol, a critical C2 symmetric pathway intermediate. Despite the power of this coupling reaction for the elegant and rapid assembly of the etoposide scaffold, dirigent proteins have not been utilized to generate other complex lignan natural products. Here, we demonstrate that dirigent proteins from Podophyllum hexandrum in combination with a laccase guide the heterocoupling of natural and synthetic coniferyl alcohol analogues for the enantioselective synthesis of pinoresinol analogues. This route for complexity generation is remarkably direct and efficient: three new bonds and four stereocenters are produced from two different achiral monomers in a single step. We anticipate our results will enable biocatalytic routes to difficult-to-access non-natural lignan analogues and etoposide derivatives. Furthermore, these dirigent protein and laccase-promoted reactions of coniferyl alcohol analogues represent new regio- and enantioselective oxidative heterocouplings for which no other chemical methods have been reported.

Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties

Two western red cedar pinoresinol-lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8- and 8′-linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can enantiospecifically metabolize different furofuran lignans with modified aromatic ring substituents, but where phenolic groups at both C4/C4′ are essential for catalysis. These results are consistent with quinone methide intermediate formation in the PLR active site. Site-directed mutagenesis and kinetic measurements provided additional insight into factors affecting enantioselectivity and kinetic properties. From these data, PLRs can be envisaged to allow for the biotechnological potential of generation of various lignan skeleta, that could be differentially “decorated” on their aromatic ring substituents, via the action of upstream dirigent proteins.

New lignans from the aerial parts of Rudbeckia laciniata

Three new furofuran lignans, (+)-4,4′-O-diangeloylpinoresinol (1), (+)-4,4′-O-diangeloylmedioresinol (2), and (+)-4,4′-O- diangeloylsyringaresinol (3), together with the known compound (+)-syringaresinol, were isolated from the MeOH extract of Rudbeckia l

The Constituents of Eucommia ulmoides OLIV. I. Isolation of (+)-Medioresinol Di-O-β-D-glucopyranoside

A new lignan diglycoside was isolated from the bark of Eucommia ulmoides OLIV. (Eucommiaceae) and its structure was established as (+)-medioresinol di-O-β-D-glucopyranoside (1) by means of chemical and spectral studies. (+)-Pinoresinol di-O-β-D-glucopyranoside (2),liriodendrin (3) and (+)-pinoresinol O-β-D-glucopyranoside (4) were also isolated.Keywords - Eucommia ulmoides; lignan; (+)-medioresinol di-O-β-D-glucoside; (+)-pinoresinol di-O-β-D-glucoside; (+)-pinoresinol O-β-D-glucoside; liriodendrin; (13)C-NMR