15896-36-3

Basic information

• Product Name: α-Hydroxynonanoic acid
• Synonyms: α-Hydroxynonanoic acid;2-Hydroxypelargonic acid
• CAS NO: 15896-36-3
• Molecular Formula: C₉H₁₈O₃
• Molecular Weight: 174.24
• Mol File: 15896-36-3.mol

Chemical Properties

• Melting Point: 70 °C
• Boiling Point: 303.9±15.0 °C(Predicted)
• Appearance: /
• Density: 1.027±0.06 g/cm3(Predicted)
• PKA: 3.86±0.21(Predicted)
• CAS DataBase Reference: α-Hydroxynonanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: α-Hydroxynonanoic acid(15896-36-3)
• EPA Substance Registry System: α-Hydroxynonanoic acid(15896-36-3)

Safety Data

• Hazardous Substances Data: 15896-36-3(Hazardous Substances Data)

Upstream product

• 145090-39-7 S-methyl-2-acetoxythiononanoate 
• 116296-93-6 2-hydroxy-nonanenitrile 
• 7425-60-7 2-bromo-n-nonanoic acid ethyl ester 
• 124-13-0 Octanal 
• 3098-30-4 α-Acetoxypelargonsaeureethylester 
• 112-05-0 nonanoic acid 
• 394213-17-3 2-bromo-nonanoyl chloride 
• 111-87-5 octanol 
• 1301234-58-1 C₁₃H₂₇NO₂ 
• 5440-35-7 2-aminononanoic acid 
• 18295-03-9 2-Hydroxy-non-4-ensaeure-butylester 
• 592-76-7 1-Heptene 
• 39267-31-7 1-methanesulfinyl-nonan-2-one 
• 111-11-5 methyl octanate 

Downstream Products

• 124-13-0 Octanal 
• 143993-00-4 2-hydroxy-nonanoic acid anilide 
• 109856-84-0 (S)-(-)-2-heptyloxirane 
• 111423-28-0 (S)-nonane-1,2-diol 
• 133444-84-5 (S)-2-amino-nonanoic acid 
• 14952-06-8 methyl (2E)-2-nonenoate 

Relevant articles and documents

Preparative Asymmetric Synthesis of Canonical and Non-canonical a-amino Acids through Formal Enantioselective Biocatalytic Amination of Carboxylic Acids

Chemical and biocatalytic synthesis of non-canonical a-amino acids (ncAAs) from renewable feedstocks and using mild reaction conditions has not efficiently been solved. Here, we show the development of a three-step, scalable and modular one-pot biocascade for linear conversion of renewable fatty acids (FAs) into enantiopure l-a-amino acids. In module 1, selective a-hydroxylation of FAs is catalyzed by the P450 peroxygenase P450CLA. By using an automated H2O2 supplementation system, efficient conversion (46 to >99%; TTN>3300) of a broad range of FAs (C6:0 to C16:0) into valuable a-hydroxy acids (a-HAs; >90% a-selective) is shown on preparative scale (up to 2.3 gL1 isolated product). In module 2, a redox-neutral hydrogen borrowing cascade (alcohol dehydrogenase/amino acid dehydrogenase) allowed further conversion of a-HAs into l-a-AAs (20 to 99%). Enantiopure l-a-AAs (e.e. >99%) including the pharma synthon l-homo-phenylalanine can be obtained at product titers of up to 2.5 gL1. Based on renewables and excellent atom economy, this biocascade is among the shortest and greenest synthetic routes to structurally diverse and industrially relevant ncAAs.

Preparative Asymmetric Synthesis of Canonical and Non-canonical α-amino Acids Through Formal Enantioselective Biocatalytic Amination of Carboxylic Acids

Chemical and biocatalytic synthesis of non-canonical α-amino acids (ncAAs) from renewable feedstocks and using mild reaction conditions has not efficiently been solved. Here, we show the development of a three-step, scalable and modular one-pot biocascade for linear conversion of renewable fatty acids (FAs) into enantiopure l-α-amino acids. In module 1, selective α-hydroxylation of FAs is catalyzed by the P450 peroxygenase P450CLA. By using an automated H2O2 supplementation system, efficient conversion (46 to >99%; TTN>3300) of a broad range of FAs (C6:0 to C16:0) into valuable α-hydroxy acids (α-HAs; >90% α-selective) is shown on preparative scale (up to 2.3 g L?1 isolated product). In module 2, a redox-neutral hydrogen borrowing cascade (alcohol dehydrogenase/amino acid dehydrogenase) allowed further conversion of α-HAs into l-α-AAs (20 to 99%). Enantiopure l-α-AAs (e.e. >99%) including the pharma synthon l-homo-phenylalanine can be obtained at product titers of up to 2.5 g L?1. Based on renewables and excellent atom economy, this biocascade is among the shortest and greenest synthetic routes to structurally diverse and industrially relevant ncAAs. (Figure presented.).

Metal-free one-pot α-carboxylation of primary alcohols

An efficient metal-free procedure for the formal α-carboxylation of primary alcohols has been developed. The method involves a one-pot oxidation/Passerini/hydrolysis sequence and provides access to α-hydroxy acids bearing a broad range of functional groups. A minor modification to the reaction conditions extends the range of accessible products to α-hydroxy esters.

A practical and inexpensive 'convertible' isonitrile for use in multicomponent reactions

N-tert-Butylamides are readily converted into the corresponding carboxylic acids by simple nitrosation. The process, which occurs under mild nonaqueous conditions, leaves carboxylic esters untouched and transforms multicomponent reaction products into useful building blocks for further synthetic elaboration.

SHORT CHAIN 2-HYDROXYCARBOXYLIC ACID-BASED DERIVATIVES OF CERAMIDES

The present invention relates to active ceramide derivatives. Specifically, the invention relates to 2(alpha)-hydroxycarboxylic acid-based ceramide derivatives. The present invention describes a method for obtaining these compounds. The invention also relates to the use of these compounds in cosmetic compositions.

Compositions and methods for enhancing the topical effects of sunscreen agents

Uses of topical compositions comprising a 2-hydroxycarboxylic acid or related compound to alleviate or improve signs of skin, nail and hair changes associated with intrinsic or extrinsic aging are disclosed. 2-Hydroxycarboxylic acids and their related compounds include, for example, 2-hydroxyethanoic acid, 2-hydroxypropanoic acid, 2-methyl 2-hydroxypropanoic acid, 2-phenyl 2-hydroxyethanoic acid, 2-phenyl 2-methyl 2-hydroxyethanoic acid, 2-phenyl 3-hydroxypropanoic acid, 2,2-diphenyl 2-hydroxyethanoic acid, 2-hydroxybutane-1,4-dioicacid, 2,3-hihydroxybutane-1,4-dioic acid, 2-carboxy 2-hydroxypentane-1,5-dioic acid, 2-ketopropanoic acid, methyl 2-ketopropanoate, ethyl 2-ketopropanoate, and gluconolactone. Topical application of compositions comprising 2-hydroxycarboxylic acid and/or related compounds has been found to alleviate or improve skin lines; blotches; blemishes; nodules; wrinkles; pigmented spots; atrophy; precancerous lesions; elastotic changes characterized by leathery, coarse, rough, dry and yellowish skin; and other skin changes associated with intrinsic aging or skin damages caused by extrinsic factors such as sunlight, radiations, air pollution, wind, cold, dampness, heat, chemicals, smoke and cigarette smoking. Topical applications of such compositions have also been found to improve the overall qualities of nail and hair affected by intrinsic aging or damaged by extrinsic factors.

Anhydrous cosmetic composition with ceramides for firming skin

A method and cosmetic composition for improving skin firmness are provided through an anhydrous composition including a hydrophobic carrier which may be a silicone or hydrocarbon for delivering an effective amount of a ceramide formed of a sphingoid base linked through an amide to a 2-hydroxycarboxylic C2-C30group.

Convenient synthesis of (±)- and (S)-antipode of (4E,7S)-7-methoxytetradec-4-enoic acid, the antimicrobial principle of marine cyanophyte

The (±)- and (S)-isomers of title compound I were prepared via a short and efficient route. The key features of the synthesis were the use of easily accessible materials, operationally simple reaction protocol and highly enantioselective lipase catalyzed esterification for the generation of the required chiron.

Cosmetic compositions for reducing or preventing signs of cellulite

The invention is directed to increasing the strength and firmness of the skin and reducing the signs of cellulite. The inventive method includes applying to the skin a composition that includes inositol phosphate, particularly phytic acid and its salts, in a cosmetically acceptable carrier.

Hydroxamic acid derivatives and pharmaceutical compositions thereof

The invention provides hydroxamic acid derivatives of the formula ψψ ψwherein R1 represents 1-7C alkyl; Ry represents hydrogen, 1-6C alkyl or a group of the formula -(CH2)n-aryl or -(CH2)n-Het in which n stands for 1-4 and Het represents a 5- or 6-membered N-heterocyclic ring which (a) is attached via the N atom, (b) optionally contains N, O and/or S as additional hetero atom(s) in a position or positions other than adjacent to the linking N atom, (c) is substituted by oxo on one or both C atoms adjacent to the linking N atom and (d) is optionally benz-fused or optionally substituted on one or more other carbon atoms by 1-6C alkyl or oxo and/or on any additional N atom(s) by 1-6C alkyl; R3 represents the characterizing group of a natural or non-natural à-amino acid in which any functional group present may be protected, with the proviso that R3 does not represent hydrogen; R4 represents carboxyl, (1-6C alkoxy)-carbonyl, carbamoyl or (1-6C alkyl)carbamoyl; R5 represents the characterizing group of a naturally occurring à-amino acid in which any functional group present may be protected; and R6 represents hydrogen; or R4, R5 and R6 each individually represent hydrogen or 1-6C alkyl, and their pharmaceutically acceptable salts, which are matrix metalloproteinase inhibitors useful for the control or prevention of degenerative joint diseases such as rheumatoid arthritis and osteoarthritis or for the treatment of invasive tumours, atherosclerosis or multiple sclerosis. They can be manufactured according to generally known methods by deprotecting a corresponding novel benzyloxyamino compound or hydroxamidating a corresponding novel amino acid or activated derivative thereof.ψ