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Coniferyl alcohol

Cat No.:V4160 Purity: ≥98%
Coniferyl alcohol is an important intermediate used in biosynthesis of eugenol and of stilbene and coumarin.
Coniferyl alcohol
Coniferyl alcohol Chemical Structure CAS No.: 458-35-5
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Coniferyl alcohol:

  • (E)-Coniferyl alcohol
Official Supplier of:
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Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Coniferyl alcohol is an important intermediate used in biosynthesis of eugenol and of stilbene and coumarin. It is also one of the preferred substrate of the eucalpytus globus enzyme and was used once as a fungal growth inhibitor

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Coniferyl alcohol alone did not elicit significant retinue attraction from worker honey bees in a laboratory bioassay. [1]
Coniferyl alcohol acted synergistically with the queen mandibular pheromone (QMP, a blend of five components: 9-ODA, 9-HDA, HOB, HVA) and other newly identified compounds (methyl oleate, hexadecan-1-ol, linolenic acid) to significantly increase retinue attraction in worker bees. The retinue activity of the combined blend (QMP + CA + others) was significantly greater than QMP alone. [1]
The activity of Coniferyl alcohol in the retinue bioassay was found to be light-sensitive when dissolved in protic solvents (e.g., methanol) under ambient fluorescent light, leading to decreased activity. [1]
ln Vivo
The study used Arabidopsis thaliana as a model plant. Infection with Verticillium longisporum led to the accumulation of coniferyl alcohol and its glucoside, coniferin, in leaves from early stages (10 days post-inoculation). A transgenic plant line overexpressing the glucosyltransferase UGT72E2 (UGT72E2-OE), which accumulates high levels of coniferin (the glucosylated form of coniferyl alcohol), showed enhanced resistance to V. longisporum infection. Infected UGT72E2-OE plants exhibited significantly less stunted growth (50% reduction in symptom severity compared to controls) and contained approximately 10 times less fungal DNA than infected wild-type plants, indicating restricted fungal proliferation [2].
Cell Assay
The antifungal activity of coniferyl alcohol was assessed using a fungal growth inhibition assay. Verticillium longisporum spores were spot-inoculated onto potato dextrose agar plates supplemented with different concentrations of the compound. Plates were incubated at 20°C in the dark for 17 days, after which the colony area was measured and compared to untreated controls to determine growth inhibition [2].
A metabolite conversion assay was performed in liquid culture. V. longisporum was grown in simulated xylem fluid medium for 7 days, then treated with 100 µM coniferyl alcohol for 24 hours. The culture medium was subsequently analyzed by UPLC-MS to identify metabolic products formed by the fungus, revealing the oxidation of coniferyl alcohol to ferulic acid [2].
Animal Protocol
Coniferyl alcohol. The bioassays described are behavioral assays using live honey bees. [1]
For the honey bee retinue bioassay: Unmated nurse worker bees were placed in a Petri dish. A lure (pseudoqueen) made from a Pasteur pipette was spotted with the test treatment (dissolved in appropriate solvent, with dose expressed as queen equivalents, Qeq). After solvent evaporation, the lure was introduced into the dish. The number of bees contacting the lure with mouthparts or antennae was recorded every 30 seconds for 5 minutes. The sum of contacts served as the bioassay score. Coniferyl alcohol was tested as part of synthetic blends. During testing of light-sensitive components, lures were prepared under red light and kept in the dark until the assay, which was conducted under dim incandescent light. [1]
ADME/Pharmacokinetics
Coniferol is present in any organism. [1]
Quantitative analysis of queen bees after mating determined that the average coniferol content per queen bee equivalent (Qeq) was 0.15 ± 0.04 µg (mean ± standard error, n=10). [1]
Toxicity/Toxicokinetics
This study evaluated the direct in vitro toxicity of coniferol to Verticillium longisporum, and the results showed that it had a growth-inhibiting effect. [2]
References

[1]. New components of the honey bee (Apis mellifera L.) queen retinue pheromone. Proc Natl Acad Sci U S A. 2003 Apr 15;100(8):4486-91.

[2]. Soluble phenylpropanoids are involved in the defense response of Arabidopsis against Verticillium longisporum. New Phytol. 2014 May;202(3):823-37.

[3]. Plant Cell Rep.2014 Aug;33(8):1263-74.

Additional Infomation
Coniferol is a phenylpropanoid compound and one of the major lignin monomers, generated by the reduction of the carboxyl group of cinnamic acid and the addition of hydroxyl and methoxy substituents to the aromatic ring. It has multiple functions, including as a lignin monomer, mouse metabolite, pheromone, animal metabolite, plant metabolite, and volatile oil component. It belongs to the phenylpropanoid class of compounds and is also a member of the guaiacol class. Its function is related to (E)-cinnamyl alcohol. Coniferol has been reported to exist in Magnolia officinalis, Paecilomyces fulvus, and other organisms with relevant data. See also: Sodium lignin (monomer); Ammonium lignin sulfonate (monomer). Calcium lignin sulfonate (20000 MW) (monomer)... See more...
Coniferol [(E)-3-(4-hydroxy-3-methoxyphenyl)-prop-2-en-1-ol] has been identified as one of four new components in the pheromone mixture of bee queens and her stalks. [1]
It is a phenylpropanoid compound. Other related phenylpropanoid compounds (ferulic acid, dihydroferulic acid, dihydroconiferol) have also been found in queen bee extracts, but they are not associated with follower attraction. [1]
Coniferol is present in the mandibular glands of queen bees after mating, but has not been detected in virgin queen bees, drones, or worker bees. [1]
Its stability depends on solvent and light; it undergoes photochemical degradation when exposed to light in protic solvents such as methanol. [1]
This compound is part of a multi-glandular synergistic pheromone mixture of at least nine compounds that can induce follower behavior in worker bees, which is crucial for queen care and the spread of pheromones within the colony. [1]
Coniferol (or similar aromatic compounds) is not a product of the mandibular glands of some other bee species (such as the Chinese honeybee and the black-banded honeybee), although they produce other 4-hydroxy-3-methoxyphenyl compounds. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H12O3
Molecular Weight
180.2005
Exact Mass
180.079
CAS #
458-35-5
Related CAS #
(E)-Coniferyl alcohol;32811-40-8
PubChem CID
1549095
Appearance
Off-white to light yellow solid powder
Density
1.198g/cm3
Boiling Point
163-165 °C3 mm Hg(lit.)
Melting Point
75-80 °C(lit.)
Flash Point
163-165°C/3mm
Vapour Pressure
6.93E-07mmHg at 25°C
Index of Refraction
1.685
LogP
1.406
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Heavy Atom Count
13
Complexity
168
Defined Atom Stereocenter Count
0
SMILES
COC1=C(C=CC(=C1)/C=C/CO)O
InChi Key
JMFRWRFFLBVWSI-NSCUHMNNSA-N
InChi Code
InChI=1S/C10H12O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-5,7,11-12H,6H2,1H3/b3-2+
Chemical Name
4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 36~100 mg/mL ( 199.77~554.94 mM )
Ethanol : ~36 mg/mL
Water : ~15 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.54 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (11.54 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (11.54 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.08 mg/mL (11.54 mM)

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.5494 mL 27.7469 mL 55.4939 mL
5 mM 1.1099 mL 5.5494 mL 11.0988 mL
10 mM 0.5549 mL 2.7747 mL 5.5494 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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