Basic information
- Standard SMILES
COc1cc(CO)ccc1O- InChIKey
ZENOXNGFMSCLLL-UHFFFAOYSA-N- Molecular formula
- C8H10O3
- Average molar mass
- 154.16 g/mol
- Monoisotopic mass
- 154.06299418
Overview
Vanillyl alcohol is a monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4. It has a role as a plant metabolite. It is a member of guaiacols and a member of benzyl alcohols.
Names & identifiers
- Preferred name
- Vanillyl alcohol
- IUPAC
- 4-(hydroxymethyl)-2-methoxyphenol
- English name
- Vanillyl alcohol
- Molecular formula
- C8H10O3
- Molecular weight
- 154.16
Names & synonyms
Vanillyl alcohol498-00-04-Hydroxy-3-methoxybenzyl alcohol4-(Hydroxymethyl)-2-methoxyphenolVanillin alcoholVanillic alcohol4-Hydroxy-3-methoxybenzenemethanolFEMA No. 3737X7EA1JUA6MNSC-3993DTXSID20198074V0018
Show more names
FEMA 3737VanillylVanillinolVANILLYL ALCOHOL(RG)4-Hydroxy-3-Methoxybenze-neMenthanol4-HYDROXY-3-METHOXYBENZYL ALCOHOL (VANILLYL ALCOHOL)
CHEBI:18353V-0018RefChem:901716DTXCID50120565207-852-4Benzenemethanol, 4-hydroxy-3-methoxy-vanillol4-Hydroxy-3-methoxyphenylmethanol
Database identifiers
- CAS
498-00-0- PubChem CID
- 62348
- DTXSID
DTXSID20198074- ChEMBL
CHEMBL4297450- ChEBI
CHEBI:18353- UNII
- X7EA1JUA6M
- EC Number
- 207-852-4
- Nikkaji
- J28.483A
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 49.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 116
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
PolymersOther Classes -> Alcohols and Polyols, Other
LogP0.420
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
2 mg/mL at 20 °C
soluble in hot water, organic solvents, oils
soluble (in ethanol)
Boiling Point
312.00 to 313.00 °C. @ 760.00 mm Hg
(decomposes at the melting point)
Melting Point114 - 115 °C
Physical Description
Off-white powder; [Alfa Aesar MSDS]
Solid
white or colourless crystals with a mild, sweet, balsamic, vanilla-like odour
Physicochemical properties
- Melting point
- 110 · 110-117 °C (lit.)
- Boiling point
- 237.52 °C · 237.52°C (rough estimate)
- Density
- 1.169 · 1.1690 (rough estimate)
- refractive index
- 1.462 · 1.4620 (estimate)
- FEMA
- 3737 · 3737 | VANILLYL ALCOHOL
- FLAVIS Number
- 2.213 · 02.213 | Vanillyl alcohol
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- soluble in Methanol
- form
- Fine Crystalline Powder
- pka
- 9.75 · 9.75±0.18(Predicted)
- color
- Off-white to beige
- Odor
- 100 % · at 100.00 %. sweet creamy vanilla caramellic coconut graham cracker tonka milky powdery
- Odor Type
- creamy
- biological source
- synthetic
- Water Solubility
- 95 % · Soluble in 95% ethanol (5 %), water, and oils.
- JECFA Number
- 886 · 886
- BRN
- 1910044 · 1910044
- Henry's Law Constant
- 9.6 · 9.6×104 mol/(m3Pa) at 25℃, McFall et al. (2020)
- Stability
- Stable. Incompatible with strong oxidizing agents, strong acids.
- InChI
- 1S/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3
- InChIKey
- ZENOXNGFMSCLLL-UHFFFAOYSA-N
- SMILES
- COc1cc(CO)ccc1O
- LogP
- 0.42 · 0.42
- Substances Added to Food (formerly EAFUS)
- VANILLYL ALCOHOL
- CAS DataBase Reference
- 498 · 498-00-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 EA1JUA6M · X7EA1JUA6M
- NIST Chemistry Reference
- 4 · 4-Hydroxy-3-methoxybenzyl alcohol(498-00-0)
- UNSPSC Code
- 12164502 · 12164502
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- HS Code
- 29095090 · 29095090
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 58.6% (82 of 140) of all reports.
Warning
H315 (40.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 140 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenemethanol, 4-hydroxy-3-methoxy
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 29-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/34654
Benzenemethanol, 4-hydroxy-3-methoxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS] See Vanillin.
Hazard Classes and CategoriesSkin Irrit. 2 (40.7%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29095090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
Description4-hydroxy-3-methoxybenzyl alcohol (also known as vanillyl alcohol) is often used as a deodorant component that is active in preventing the formation of body odor. It can also be used as a flavoring agent. Recent studies have also demonstrated that it has certain pharmacological effects. For example, it has been confirmed that it has certain neuro-protective effects through suppressing the oxidative stress and anti-apoptotic activity in toxin-induced dopaminergic MN9D cells, making it a potential candidate for the treatment of neurodegenerative diseases such as Parkinson’s disease.
UsesUsed as a flavoring agent. Other possible uses, vanilla, coconut, cream and other dairy nuances, coumarin.
General DescriptionVanillyl alcohol belongs to the phenolic group of compounds which are widely used as oxidants in food products.
Upstream & downstream products
Downstream products
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes
DefinitionChEBI: Vanillyl alcohol is a monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4. It has a role as a plant metabolite. It is a member of guaiacols and a member of benzyl alcohols.
Related reactions
31 records
Linked notes
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