Page last updated: 2024-12-08

(2S,3R)-dihydrodehydrodiconiferyl alcohol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

You're asking about **(2S,3R)-dihydrodehydrodiconiferyl alcohol**, which is a complex organic molecule with an intriguing history and potential applications. Here's a breakdown:

**What it is:**

* **Structure:** It's a dimer (two units joined together) of coniferyl alcohol, a building block for lignin, a key structural component of plant cell walls.
* **Stereochemistry:** The (2S,3R) designation refers to the specific arrangement of atoms around two chiral centers in the molecule. This stereochemistry is crucial, as it affects the molecule's interaction with other molecules.
* **Origin:** It's a natural product found in various plant species, particularly in wood.
* **Properties:** It's a colorless, crystalline solid with specific optical properties due to its chirality.

**Why it's important for research:**

1. **Lignin Biodegradation:** (2S,3R)-dihydrodehydrodiconiferyl alcohol is a key intermediate in the breakdown of lignin by certain fungi and bacteria. Understanding its role in this process could lead to new strategies for:
* **Biofuel Production:** Breaking down lignin in plant biomass could unlock sugars for biofuel production.
* **Sustainable Materials:** Degrading lignin could enable the production of bio-based polymers and other materials.

2. **Plant Cell Wall Research:** The molecule's structure provides insights into the complex and dynamic nature of plant cell walls. This understanding can help us:
* **Improve Plant Growth:** Develop methods to manipulate cell wall structure for better crop yields and disease resistance.
* **Biotechnology Applications:** Utilize the knowledge of plant cell wall assembly and degradation for new biomaterials and pharmaceuticals.

3. **Medicinal Chemistry:** The molecule and its analogs have shown potential biological activity, including:
* **Antioxidant Properties:** Its structure suggests potential for scavenging free radicals, protecting cells from damage.
* **Antimicrobial Activity:** Research suggests it might have inhibitory effects against certain bacteria and fungi.

**Ongoing Research:**

Active research focuses on:

* **Enzymatic Degradation of Lignin:** Investigating the enzymes involved in lignin breakdown and their interaction with this molecule.
* **Synthesis and Modification:** Developing new methods for synthesizing the molecule and its analogs for further research.
* **Biological Activity Testing:** Evaluating the molecule's potential as a therapeutic agent and understanding its mechanisms of action.

**Overall, (2S,3R)-dihydrodehydrodiconiferyl alcohol is a fascinating molecule with significant potential applications in various fields, from sustainable materials to medicine. Continued research promises to uncover more about its properties and unlock new possibilities.**

Cross-References

ID SourceID
PubMed CID384679
CHEMBL ID261907
CHEBI ID143257

Synonyms (19)

Synonym
NCI60_026519
nsc674906
nsc-674906
dihydrodehydrodiconiferyl alcohol
sblzvjihpwrsqq-hnayvobhsa-
inchi=1/c20h24o6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h5-6,8-10,15,19,21-23h,3-4,7,11h2,1-2h3/t15-,19+/m0/s1
4-[(2s,3r)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
dihydrodehydrodiconifery alcohol
(+)-dihydrodehyrodiconiferyl alcohol
(7s,8r)-dihydrodehydrodiconiferyl alcohol
CHEMBL261907
CHEBI:143257
(2s,3r)-dihydrodehydrodiconiferyl alcohol
28199-69-1
FS-9708
5-benzofuranpropanol,2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-, (2s-trans)-
XD172959
DTXSID501272203
AKOS040761622
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
1-benzofuransA member of the class of benzofurans consisting of a 1-benzofuran skeleton and its substituted derivatives thereof.
guaiacolsAny phenol carrying an additional methoxy substituent at the ortho-position.
guaiacyl ligninLignin composed principally of coniferol (guaiacyl) units.
primary alcoholA primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID775187Cytotoxicity against mouse RAW264.7 cells assessed as cell viability by colorimetric method relative to control2013Bioorganic & medicinal chemistry letters, Nov-01, Volume: 23, Issue:21
Anti-inflammatory constituents from the fruits of Vitex rotundifolia.
AID591311Antiinflammatory activity in mouse BV2 cells assessed as inhibition of lipopolysaccharide induced NO production2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID738973Antiviral activity against Hepatitis B virus infected in human HepG2.2.15 cells assessed as inhibition of HBsAg secretion after 12 days by ELISA2013Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7
Anti-hepatitis B virus lignans from the root of Streblus asper.
AID591307Anticancer activity against human SKOV3 cells by SRB assay2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID738972Cytotoxicity against human HepG2(2.2.15) cells after 12 days by MTT assay2013Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7
Anti-hepatitis B virus lignans from the root of Streblus asper.
AID591310Anticancer activity against human XF498 cells by SRB assay2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID1552788Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS/IFNgamma-induced NO production by measuring NO level preincubated for 2 hrs and followed by LPS/IFNgamma addition and measured after 24 hrs by Griess assay2019Bioorganic & medicinal chemistry letters, 09-01, Volume: 29, Issue:17
Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities.
AID262264Cytotoxicity against HT1080 cells at 1.0 uM after 72 hrs2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.
AID590972Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells preincubated with compound for 1 hr before exposure to LPS measured after 24 hrs by Griess reaction method2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 macrophage cells by lignans isolated from Euonymus alatus leaves and twigs.
AID591309Anticancer activity against human SK-MEL-2 cells by SRB assay2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID738969Antiviral activity against Hepatitis B virus infected in human HepG2.2.15 cells assessed as inhibition of HBeAg secretion after 12 days by ELISA2013Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7
Anti-hepatitis B virus lignans from the root of Streblus asper.
AID262256Cytotoxicity against B16F10 cells at 10 uM after 72 hrs2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.
AID262240Cytotoxicity against U937 cells at 1.0 uM after 72 hrs2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.
AID1552786Inhibition of electric eel AChE using acetylthiocholine iodide as substrate pretreated for 15 mins followed by substrate addition and measured after 60 mins by Ellman's method2019Bioorganic & medicinal chemistry letters, 09-01, Volume: 29, Issue:17
Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities.
AID262241Cytotoxicity against U937 cells at 10 uM after 72 hrs2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.
AID591308Anticancer activity against human A549 cells by SRB assay2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID262255Cytotoxicity against B16F10 cells at 1.0 uM after 72 hrs2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.
AID1754175Antiinflammatory activity in mouse RAW264.7 assessed as inhibition of LPS-induced NO production preincubated for 30 mins followed by LPS stimulation measured after 24 hrs by Griess reagent based assay2021Journal of natural products, 05-28, Volume: 84, Issue:5
Tulipiferamide A, an Alkamide from
AID775188Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production after 24 hrs by Griess method2013Bioorganic & medicinal chemistry letters, Nov-01, Volume: 23, Issue:21
Anti-inflammatory constituents from the fruits of Vitex rotundifolia.
AID262254Cytotoxicity against B16F10 cells at 0.1 uM after 72 hrs2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.
AID262263Cytotoxicity against HT1080 cells at 0.1 uM after 72 hrs2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.
AID262265Cytotoxicity against HT1080 cells at 10 uM after 72 hrs2006Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6
Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.
AID738968Antiviral activity against Hepatitis B virus infected in human HepG2.2.15 cells assessed as inhibition of HBV DNA replication after 72 hrs by PCR analysis2013Bioorganic & medicinal chemistry letters, Apr-01, Volume: 23, Issue:7
Anti-hepatitis B virus lignans from the root of Streblus asper.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's5 (71.43)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.16

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index13.16 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index5.24 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.16)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]