Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H18O7 |
| Molecular Weight | 286.2778 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@@H](OC2=C(CO)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=NGFMICBWJRZIBI-UJPOAAIJSA-N
InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
| Molecular Formula | C13H18O7 |
| Molecular Weight | 286.2778 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25907238
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25907238
The most well known component of willow bark extract is salicin, it is a prodrug, which is gradually transported to the lower part of the intestine, hydrolyzed to saligenin by intestinal bacteria, and converted to salicylic acid after absorption. Salicin possesses an analgesic, anti-inflammatory, and antipyretic properties. Salicin suppressed the activation of MAPKs and NF-κB signaling pathways and thus maybe might be a potential therapeutic agent against inflammatory diseases.
Approval Year
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
99 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11599656 |
240 mg single, oral dose: 240 mg route of administration: Oral experiment type: SINGLE co-administered: |
SALICYLIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
10.7 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11599656 |
240 mg single, oral dose: 240 mg route of administration: Oral experiment type: SINGLE co-administered: |
N-SALICYLOYLGLYCINE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.9 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11599656 |
240 mg single, oral dose: 240 mg route of administration: Oral experiment type: SINGLE co-administered: |
GENTISIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11599656 |
240 mg single, oral dose: 240 mg route of administration: Oral experiment type: SINGLE co-administered: |
SALICYLIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sugarcane ShSUT1: analysis of sucrose transport activity and inhibition by sucralose. | 2006-10 |
|
| Temporal coding mediates discrimination of "bitter" taste stimuli by an insect. | 2006-08-30 |
|
| Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada. | 2006-08-07 |
|
| Conflicting demands on detoxification pathways influence how common brushtail possums choose their diets. | 2006-08 |
|
| Allergy-preventive phenolic glycosides from Populus sieboldii. | 2006-08 |
|
| Arabidopsis thaliana beta-Glucosidases BGLU45 and BGLU46 hydrolyse monolignol glucosides. | 2006-08 |
|
| Monitoring carbohydrate enzymatic reactions by quantitative in vitro microdialysis. | 2006-06-16 |
|
| [The Italian contributions to the history of salicylates]. | 2006-04-28 |
|
| Herbal medicine for low back pain. | 2006-04-19 |
|
| Cloning and comparison of third beta-glucoside utilization (bglEFIA) operon with two operons of Pectobacterium carotovorum subsp. carotovorum LY34. | 2006-04 |
|
| The historical analysis of aspirin discovery, its relation to the willow tree and antiproliferative and anticancer potential. | 2006-04 |
|
| The expression of genes encoding lipodepsipeptide phytotoxins by Pseudomonas syringae pv. syringae is coordinated in response to plant signal molecules. | 2006-03 |
|
| Inhibition activities of natural products on serine proteases. | 2006-03 |
|
| Reclassification of Paenibacillus larvae subsp. pulvifaciens and Paenibacillus larvae subsp. larvae as Paenibacillus larvae without subspecies differentiation. | 2006-03 |
|
| Genomic variation in Streptococcus mutans: deletions affecting the multiple pathways of beta-glucoside metabolism. | 2006-02 |
|
| Metabolic pathways variability and sequence/networks comparisons. | 2006-01-18 |
|
| Osteoarthritis and nutrition. From nutraceuticals to functional foods: a systematic review of the scientific evidence. | 2006 |
|
| HPLC-MS/MS analysis of willow bark extracts contained in pharmaceutical preparations. | 2005-12-01 |
|
| Purification and characterization of an intracellular beta-glucosidase from the methylotrophic yeast Pichia pastoris. | 2005-12 |
|
| Electrophysiological and behavioural characterization of gustatory responses to antennal 'bitter' taste in honeybees. | 2005-12 |
|
| Stable isotope characterization of the ortho-oxygenated phenylpropanoids: coumarin and melilotol. | 2005-11-30 |
|
| Pyrosequencing Bacillus anthracis. | 2005-10 |
|
| Purification and characterization of two endo-beta-1,4-glucanases from mollusca, Ampullaria crossean. | 2005-10 |
|
| Genetic variability among Blastoschizomyces capitatus isolates from different clinical sources. | 2005-09-17 |
|
| Lactobacillus concavus sp. nov., isolated from the walls of a distilled spirit fermenting cellar in China. | 2005-09 |
|
| Analysis of carbohydrates in plants by high-performance anion-exchange chromatography coupled with electrospray mass spectrometry. | 2005-08-26 |
|
| Aerococcus urinae: polyphasic characterization of the species. | 2005-08-10 |
|
| A digestive beta-glucosidase from the silkworm, Bombyx mori: cDNA cloning, expression and enzymatic characterization. | 2005-08 |
|
| Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae). | 2005-07-27 |
|
| Positive selection on a high-sensitivity allele of the human bitter-taste receptor TAS2R16. | 2005-07-26 |
|
| [Purification of lectin from perch (Persa fluviatilis L.) roe specific to cellobiose and study of its characteristics]. | 2005-05-25 |
|
| Semi-industrial isolation of salicin and amygdalin from plant extracts using slow rotary counter-current chromatography. | 2005-05-13 |
|
| Comparison of molecular mobility in the glassy state between amorphous indomethacin and salicin based on spin-lattice relaxation times. | 2005-05 |
|
| Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction. | 2005-04-20 |
|
| Emergence of unusual species of enterococci causing infections, South India. | 2005-03-17 |
|
| [Arbutin, salicin: the possibilities of their biotechnological production]. | 2005-03 |
|
| Structural and biochemical analysis of the asc operon encoding 6-phospho-beta-glucosidase in Pectobacterium carotovorum subsp. carotovorum LY34. | 2005-03 |
|
| Purification and characterization of recombinant Escherichia coli-expressed Pichia etchellsii beta-glucosidase II with high hydrolytic activity on sophorose. | 2005-02 |
|
| Emetic toxin formation of Bacillus cereus is restricted to a single evolutionary lineage of closely related strains. | 2005-01 |
|
| Mechanisms involved in the anti-inflammatory effect of a standardized willow bark extract. | 2005 |
|
| Sample pretreatment and determination of non steroidal anti-inflammatory drugs (NSAIDs) in pharmaceutical formulations and biological samples (blood, plasma, erythrocytes) by HPLC-UV-MS and micro-HPLC. | 2005 |
|
| Differentiation of extractive and synthetic salicin. The 2H aromatic pattern of natural 2-hydroxybenzyl alcohol. | 2004-12-29 |
|
| Purification and characterization of an extracellular b-glucosidase with high transglucosylation activity and stability from Aspergillus niger No. 5.1. | 2004-12 |
|
| Bitter taste receptors for saccharin and acesulfame K. | 2004-11-10 |
|
| Analysis of bgl operon structure and characterization of beta-glucosidase from Pectobacterium carotovorum subsp. carotovorum LY34. | 2004-11 |
|
| A randomized double-blind placebo-controlled clinical trial of a product containing ephedrine, caffeine, and other ingredients from herbal sources for treatment of overweight and obesity in the absence of lifestyle treatment. | 2004-11 |
|
| [Life threatening intestinal bleeding in a Bearded Collie associated with a food supplement for horses]. | 2004-10 |
|
| Isolation and characterization of a cellulolytic Geobacillus thermoleovorans T4 strain from sugar refinery wastewater. | 2004-10 |
|
| The role of carboxyl, guanidine and imidazole groups in catalysis by a midgut trehalase purified from an insect larvae. | 2004-10 |
|
| Sympodiomyces attinorum sp. nov., a yeast species associated with nests of the leaf-cutting ant Atta sexdens. | 2004-09 |
Sample Use Guides
for rats (fever): Orally administered SL (SALICIN) did not affect the rectal temperatures at a dose of 5 mmol/kg
for mice (colitis): 100 and 200 mg per body weight was administered daily through oral gavage for 7 days
Route of Administration:
Other
In Vitro Use Guide
Curator's Comment: It was evaluated the effect of D(-)-Salicin on cytokines (TNF-α, IL-1β, IL-6 and IL-10) in vivo and in vitro by enzyme-linked immunosorbent assay.The results showed that D(-)-Salicin markedly decreased TNF-α, IL-1β and IL-6 concentrations and increased IL-10 concentration.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:33:19 GMT 2025
by
admin
on
Mon Mar 31 18:33:19 GMT 2025
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| Record UNII |
4649620TBZ
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C241
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DSLD |
2450 (Number of products:17)
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| Code System | Code | Type | Description | ||
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CHEMBL462997
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4649620TBZ
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36100
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205-331-6
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17814
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5751
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100000078369
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439503
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DTXSID10883326
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1607903
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SALICIN
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m9730
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4649620TBZ
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138-52-3
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C90648
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C005696
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SUB15176MIG
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