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4-hydroxymethyl-pyridine

4-hydroxymethyl-pyridine is a chemical compound known as 4-pyridylcarbinol with applications mostly outside fragrances or flavors.
Chemical Structure

General Material Description

4-hydroxymethyl-pyridine, also known by its trivial name 4-pyridinemethanol, is an organic compound featuring a pyridine ring substituted with a hydroxymethyl group at the 4-position. It is classified as a heterocyclic aromatic amine alcohol with the molecular formula C6H7NO and molecular weight approximately 109.13 g/mol. The compound is known under various synonyms including 4-picolyl alcohol and gamma-picolyl alcohol. It exhibits a hazelnut-coffee-like odor, but despite this sensory property, it is primarily used for informational and research purposes rather than as a flavor or fragrance additive. Repositories such as PubChem document its chemical characteristics and structural information. 4-hydroxymethyl-pyridine can be sourced or synthesized for chemical applications where the hydroxymethyl functional group on the pyridine ring is utilized.

Occurrence, Applicability & Potential Uses

While 4-hydroxymethyl-pyridine does not naturally occur in biological systems, it serves a role in synthetic chemistry and potentially as an intermediate in pharmaceutical and chemical manufacturing. Its aromatic heterocyclic structure linked with a primary alcohol group makes it suitable for research in coordination chemistry or as a building block for more complex molecules. Regulatory frameworks such as REACH (EU) cover its production and use, emphasizing the need for documentation and safety data despite its limited direct application. Its lack of usage in flavors or fragrances distinguishes it from other pyridine derivatives, and its application remains primarily informational or experimental.

Physico-Chemical Properties Summary

4-hydroxymethyl-pyridine exhibits a molecular weight of 109.13 g/mol with the formula C6H7NO. It demonstrates low volatility, with a vapor pressure of about 0.026 mmHg at 20 °C indicating limited evaporation under ambient conditions. The flash point is relatively high, around 230 °F (approximately 110 °C), reflecting moderate thermal stability. Its log P value is near zero (0.06), which indicates balanced hydrophilic and lipophilic characteristics, consistent with its high water solubility exceeding 1,000,000 mg/L at 20 °C. These properties suggest it dissolves readily in aqueous environments and is less likely to bioaccumulate. Such physicochemical behavior influences its handling, storage, and potential incorporation in aqueous chemical formulations.

FAQ

What is 4-hydroxymethyl-pyridine and what are its main synonyms?
4-hydroxymethyl-pyridine is an organic compound consisting of a pyridine ring substituted with a hydroxymethyl group at the 4-position. It is also known as 4-pyridinemethanol, 4-picolyl alcohol, and gamma-picolyl alcohol among other synonyms. The molecule is used mainly in chemical research contexts rather than commercial flavor or fragrance applications.
How is 4-hydroxymethyl-pyridine typically used and what standards apply to its regulation?
The compound is primarily used for informational and research purposes and does not find significant application in fragrances or flavors. It is regulated under chemical safety standards such as REACH (European Union), which manage its production, documentation, and safe handling. There are no widespread consumer uses, and safety data focus on toxicity and environmental impact rather than direct use in consumer products.
Where can safety data and regulatory information for 4-hydroxymethyl-pyridine be accessed?
Safety data for 4-hydroxymethyl-pyridine are available through various public chemical databases such as the European Chemicals Agency (ECHA), which provides REACH registration details. Additional information can be found in the National Institute of Allergy and Infectious Diseases database and the EPA’s Substance Registry Services. Material Safety Data Sheets (MSDS) are accessible from chemical suppliers and online repositories, detailing potential hazards and safe handling guidelines.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

pyridin-4-ylmethanol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):11472
Pubchem (sid):134975976
Publications by US Patents
3,952,024 - Furfurylthioacetone
Certain 2,5-dimethyl-3-thiopyrazines
Publications by PubMed
The role of p53 in the cellular toxicity by active trans-platinum complexes containing isopropylamine and hydroxymethylpyridine.
Study by HPLC-MS of the interaction of platinum antitumor complexes with potato carboxypeptidase inhibitor (PCI).
Influence of the position of substituents in the cytotoxic activity of trans platinum complexes with hydroxymethyl pyridines.
Selective intracellular accumulation of the major metabolite issued from the activation of the prodrug ethionamide in mycobacteria.
Chelation-assisted transformation: synthesis of 1,4-dicarboxylate esters by the Rh-catalyzed carbonylation of internal alkynes with pyridin-2-ylmethanol.
Synthesis and anti-HIV-1 and anti-HCMV activity of 1-substituted 3-(3,5-dimethylbenzyl)uracil derivatives.
Recognition of DNA modified by trans-[PtClNH(4-hydroxymethylpyridine)] by tumor suppressor protein p53 and character of DNA adducts of this cytotoxic complex.
Synthesis, characterization and biological activity of trans-platinum(II) and trans-platinum(IV) complexes with 4-hydroxymethylpyridine.
The thermal and light induced spin transition in [FeL2](BF4)2 (L = 2,6-dipyrazol-1-yl-4-hydroxymethylpyridine).
On the formation of isopropylidenepyridoxines. A convenient method for the preparation of 2,2,8-trimethyl-4H-1,3-dioxino[4,5-c]pyridin-5-ylmethanol from pyridoxine hydrochloride.
[Pharmacodynamic study of (M-14012-4) N-(4-picolyl)-3,5-dimethylbenzamide].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.39.9100
ChemSpider:View

General Material Information

Preferred name 4-hydroxymethyl-pyridine
Trivial Name 4-Pyridinemethanol
Short Description 4-pyridylcarbinol
Formula C6 H7 N O
CAS Number 586-95-8
ECHA Number 209-590-6
FDA UNII Search
Nikkaji Number J85.689D
Beilstein Number 107850
MDL MFCD00006442
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • 4-hydroxymethyl pyridine
  • 4-( hydroxymethyl)pyridine
  • 4-hydroxymethylpyridine
  • 4-picolyl alcohol
  • gamma- picolyl alcohol
  • 4-pyridin-4-ylmethanol
  • 4-pyridinecarbinol
  • 4-pyridinemethanol
  • 4-pyridyl carbinol
  • 4-pyridylcarbinol
  • 4-pyridylmethanol
  • pyridin-4-ylmethanol
  • 4-Pyridinemethanol
  • 4-(Hydroxymethyl)pyridine
  • 4-Pyridylcarbinol
  • 4-Pyridylmethanol
  • γ-Picolyl alcohol
  • 4-Pyridinecarbinol
  • 4-Picolyl alcohol
  • 4-Pyridylmethyl alcohol
  • (Pyridin-4-yl)methanol
  • NSC 126907
  • NSC 26024
  • NSC 49167
  • 4-(Hydroxymethylene)pyridine

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 109.12799072266
Vapor Pressure 0.026 mmHg @ 20 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 0.06
Solubility
water, 1.00E+06 mg/L @ 20 °C (exp) Yes

Organoleptic Properties

Flavor Type: Hazelnut
hazelnut, coffee, nutty
General comment Hazelnut- coffee-like

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-bird - wild LD50 422 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

intravenous-mouse LD50 1000 mg/kg
Pharmazie. Vol. 11, Pg. 242, 1956.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
information only not used for fragrances or flavors
Recommendation for 4-hydroxymethyl-pyridine usage levels up to:
not for fragrance use.
Recommendation for 4-hydroxymethyl-pyridine flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):586-95-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11472
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
pyridin-4-ylmethanol
Chemidplus:0000586958
RTECS:UT4691000 for cas# 586-95-8