o-Vanillin (2-Vanillin) is a naturally occurring compound found in the fruit of Vanilla planifolia, Pinus koraiensis. o-Vanillin is an effective antifungal agent. o-Vanillin inhibits hyphal growth by disrupting the integrity of cell walls and membranes. o-Vanillin inhibits NF-κB activation induced by Doxorubicin and 4-hydroperoxycyclophosphamide.

Physicochemical Properties

Molecular Formula	C8H8O3
Molecular Weight	152.15
Exact Mass	152.047
CAS #	148-53-8
PubChem CID	8991
Appearance	Typically exists as solid at room temperature
Density	1.2±0.1 g/cm3
Boiling Point	265.5±0.0 °C at 760 mmHg
Melting Point	40-42 °C(lit.)
Flash Point	94.0±15.3 °C
Vapour Pressure	0.0±0.5 mmHg at 25°C
Index of Refraction	1.588
LogP	1.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Heavy Atom Count	11
Complexity	135
Defined Atom Stereocenter Count	0
SMILES	O(C([H])([H])[H])C1=C([H])C([H])=C([H])C(C([H])=O)=C1O[H]
InChi Key	JJVNINGBHGBWJH-UHFFFAOYSA-N
InChi Code	InChI=1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3
Chemical Name	2-hydroxy-3-methoxybenzaldehyde
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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	o-Vanillin (2-Vanillin; 0-125 μg/mL; 24-72 h) prevents A from growing mycelially. flavus in a way that is dependent on dose[1]. o-Vanillin (0-100 μg/mL; 48 h; A. flavus) alters mycelial shape and causes uneven mycelial shrinkage[1]. o-Vanillin (0-100 μg/mL; A. flavus) reduces the amount of β-1,3-glucan and protein on the surface of the cell wall[1]. o-Vanillin (0-100 μg/mL; A. flavus) degrades the integrity of cell membranes. o-Vanillin lowers the pH level outside of cells and releases components of cells[1]. o-Vanillin (0–100 μg/mL) could successfully stop A from growing. flavus on kernels of corn[1]. o-In A375/NFĸB-Luc cells, vanillin (0-250 μM) suppresses doxorubicin-mediated induction of NFĸB activity by 65%. o-Vanillin reduces the activity generated by 4-HC by 43%[2].
ln Vivo	In mice with A375 human melanoma xenografts, o-vanillin (2-Vanillin; 60 mg/kg; po; daily, for 5 d) suppresses tumor growth[2].
Animal Protocol	Animal/Disease Models: Male NSG mice with A375 human melanoma xenografts (12-16 weeks of age)[2] Doses: 60 mg/kg Route of Administration: Oral administration; daily, for 5 days Experimental Results: Delayed the growth of A375 human melanoma xenografts in immunodeficient NSG mice.
References	[1]. Li Q, et, al. o-Vanillin, a promising antifungal agent, inhibits Aspergillus flavus by disrupting the integrity of cell walls and cell membranes. Appl Microbiol Biotechnol. 2021 Jun;105(12):5147-5158. [2]. Marton A, et, al. Vanillin Analogues o-Vanillin and 2,4,6-Trihydroxybenzaldehyde Inhibit NFĸB Activation and Suppress Growth of A375 Human Melanoma. Anticancer Res. 2016 Nov;36(11):5743-5750.
Additional Infomation	Ortho-vanillin is a member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3. It has a role as an antimutagen and a plant metabolite. It is a member of benzaldehydes and a member of guaiacols. It is functionally related to a salicylaldehyde. 2-Hydroxy-3-methoxybenzaldehyde has been reported in Strychnos cathayensis, Hyssopus officinalis, and Panax ginseng with data available.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL (657.25 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	6.5725 mL	32.8623 mL	65.7246 mL
	5 mM	1.3145 mL	6.5725 mL	13.1449 mL
	10 mM	0.6572 mL	3.2862 mL	6.5725 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.