The sole producer of wood-based vanillin is the company Borregaard located in Sarpsborg, Norway. View information & documentation regarding Vanillyl alcohol, including CAS, MSDS & more. National Institute for Occupational Safety and Health, "Chiral 2-alkylbranched acids, esters and alcohols. It has a role as a plant metabolite. The branching in 2-ethylhexanol inhibits its crystallization due to packing disruption; this results in a very low freezing point. As harvested, the green seed pods contain vanillin in the form of its β-D-glucoside; the green pods do not have the flavor or odor of vanilla.[25]. It is also found in Leptotes bicolor, a species of orchid native to Paraguay and southern Brazil,[13] and the Southern Chinese red pine. While the exact route of vanillin biosynthesis in V. planifolia is currently unknown, several pathways are proposed for its biosynthesis. [4] It is also used in the flavor industry, as a very important key note for many different flavors, especially creamy profiles such as cream soda. At 700 USD/kg, this product, sold under the trademarked name Rhovanil Natural, is not cost-competitive with petrochemical vanillin, which sells for around 15 USD/kg. [7], By the late 19th century, semisynthetic vanillin derived from the eugenol found in clove oil was commercially available. The para position of the ring is then hydroxylated by the cytochrome P450 enzyme cinnamate 4-hydroxylase (C4H/P450) to create p-coumaric acid. Council of Europe no. Vanillyl alcohol is derived from vanillin. Although isooctanol (and the derived isooctyl prefix) is commonly used in industry to refer to 2-ethylhexanol and its derivatives, IUPAC naming conventions[11] dictate that this name is properly applied to another isomer of octanol, 6-methylheptan-1-ol. [12] However, unlike vanillin synthesized from lignin or guaiacol, it can be labeled as a natural flavoring. Date s. Modify. Vanillin is most prominent as the principal flavor and aroma compound in vanilla. Vanillin MW 152.15 C. 8. It is used to flavor food. PubChem Substance ID 24901864. About 2,500,000 tons are prepared in this way annually. Density: 1.2±0.1 g/cm 3: Boiling Point: 313.1±27.0 °C at 760 mmHg Vapour Pressure: 0.0±0.7 mmHg at 25°C Enthalpy of Vaporization: 58.5±3.0 kJ/mol Flash Point: 143.2±23.7 °C Index of Refraction: Vanillyl alcohol ≥98%, FG Synonym: 4-Hydroxy-3-methoxybenzyl alcohol, NSC 3993, Vanillyl alcohol CAS Number 498-00-0. Because the microbe is a processing aid, the resulting vanillin would not fall under U.S. GMO labeling requirements, and because the production is nonpetrochemical, food using the ingredient can claim to contain "no artificial ingredients". MSDS: Chinese USA: Flash Point: 143.2±23.7 °C: Symbol: GHS07: Signal Word: Warning All the chemicals were used as received without further purification or treatment. [30] Later it was synthesized from lignin-containing "brown liquor", a byproduct of the sulfite process for making wood pulp. During this process, the pods become dark brown, and enzymes in the pod release vanillin as the free molecule. [31], At present, the most significant of these is the two-step process practiced by Rhodia since the 1970s, in which guaiacol (1) reacts with glyoxylic acid by electrophilic aromatic substitution. 690 . After being harvested, their flavor is developed by a months-long curing process, the details of which vary among vanilla-producing regions, but in broad terms it proceeds as follows: First, the seed pods are blanched in hot water, to arrest the processes of the living plant tissues. [6] Tiemann and Haarmann founded a company Haarmann and Reimer (now part of Symrise) and started the first industrial production of vanillin using their process in Holzminden, Germany. It is the primary component of the extract of the vanilla bean. It differs from vanillin by having an ethoxy group (−O−CH2CH3) instead of a methoxy group (−O−CH3). O + OH OCH. HCT then exchanges the shikimate/quinate for CoA to create caffeoyl CoA, and 4CL removes CoA to afford caffeic acid. Reduction of Vanillin to Vanillyl Alcohol . [8], 2-Ethylhexanol exhibits low toxicity in animal models, with LD50 ranging from 2-3 g/kg (rat). 2-Ethylhexanol (abbreviated 2-EH) is a branched, eight-carbon chiral alcohol.It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. InChI=1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3, Except where otherwise noted, data are given for materials in their. 4, NaOH 2. Vanillin is an organic compound with the molecular formula C8H8O3. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring agent in foods, beverages, and pharmaceuticals. Caffeic acid then undergoes methylation by caffeic acid O-methyltransferase (COMT) to give ferulic acid. Vanillin was first synthesized from eugenol (found in oil of clove) in 1874–75, less than 20 years after it was first identified and isolated. Vanillin has been used as a chemical intermediate in the production of pharmaceuticals, cosmetics, and other fine chemicals. Vanillin, 1 Vanillyl alcohol, 2 4 (3) Either LiAlH4 and NaBH4 could be used for this reduction, but sodium borohydride is the reagent of choice for this reaction because it is safer and easier to use. Physical and chemical properties Physical State Powder Solid Appearance Off-white Odor sweet Odor Threshold No information available pH 4.3 10 g/L (20°C) Melting Point/Range 81 - 84 °C / 177.8 - 183.2 °F Boiling Point/Range 170 °C / 338 °F @ 15 mmHg Flash Point 147 °C / 296.6 °F Evaporation Rate Not applicable H. 8. O. H O OCH. Vanillyl alcohol CAS Number: 498-00-0: Molecular Weight: 154.163: Density: 1.2±0.1 g/cm3: Boiling Point: 313.1±27.0 °C at 760 mmHg: Molecular Formula: C 8 H 10 O 3: Melting Point: 110-117 °C(lit.) [42] They may be allergic to synthetically produced vanilla but not to natural vanilla, or the other way around, or to both. Most facilities make n-butanol and isobutanol in addition to 2-ethylhexanol. Additionally, vanillin can be used as a general-purpose stain for visualizing spots on thin-layer chromatography plates. Sigma-Aldrich offers a number of Vanillin products. 3. Beilstein/REAXYS Number 1910044 . It is produced on a massive scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. [6][7], The n-butyraldeheyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully integrated facility. [28], The demand for vanilla flavoring has long exceeded the supply of vanilla beans. Not necessarily, though alcohols are incredibly versatile and useful raw materials for organic synthesis. Vanillin biosynthesis is generally agreed to be part of the phenylpropanoid pathway starting with L-phenylalanine,[27] which is deaminated by phenylalanine ammonia lyase (PAL) to form t-cinnamic acid. Vanillin is an organic compound with the molecular formula C8H8O3. Reduction of Vanillin to Vanillyl Alcohol . [3] 2-Ethylhexanol has been identified as a cause of indoor air quality related health problems, such as respiratory system irritation, as a volatile organic compound. H. 3. Today, artificial vanillin is made either from guaiacol or lignin. Vanillin Not listed LC50: 53 - 88 mg/L/96 h (Pimephales promelas) EC50 = 179 mg/L 210 minEC50: = 180 mg/L, 24h (Daphnia magna) Persistence and DegradabilityPersistence is unlikely Bioaccumulation/ AccumulationNo information available. [44], InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,8H,1H3, InChI=1/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3, Except where otherwise noted, data are given for materials in their, "Vanilla Production: Technological, Chemical, and Biosynthetic Aspects", "Recherches sur le principe odorant de la vanille", "Vanillin: Synthetic Flavoring from Spent Sulfite Liquor", "Ueber eine neue Bildungsweise aromatischer Aldehyde", "Ueber das Coniferin und seine Umwandlung in das aromatische Princip der Vanille", "Vanillin Biosynthesis – Not as simple as it seems? Preparation and stereospecific flavour evaluation", https://berrymanchemical.com/blog/2-ethylhexanol/, International Journal of Hygiene and Environmental Health, National Institute for Occupational Safety and Health (NIOSH), https://en.wikipedia.org/w/index.php?title=2-Ethylhexanol&oldid=976623023, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Chemical articles with multiple PubChem CIDs, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, 180 to 186 °C; 356 to 367 °F; 453 to 459 K, This page was last edited on 4 September 2020, at 01:21. OH 1. 2-Ethylhexanol can also be used as a cetane number booster when reacted with nitric acid. EC Number 207-852-4. It is a phenolic aldehyde. Several methods have been described for curing vanilla in days rather than months, although they have not been widely developed in the natural vanilla industry,[26] with its focus on producing a premium product by established methods, rather than on innovations that might alter the product's flavor profile.