Isolation of natural arachidonic acid as its methyl ester View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1951-02

AUTHORS

S. F. Herb, R. W. Riemenschneider, Jeanette Donaldson

ABSTRACT

Fresh beef suprarenal glands were ground and extracted thoroughly with alcohol and then with ethyl ether. After removal of solvent the total lipid residue was saponified, and the fatty acids were recovered by extraction. The less unsaturated acids were removed by crystallization from acetone at −40°C. At this stage the filtrate contained essentially all the arachidonic acid originally present in the glands and also unsaponifiable matter. After the unsaponifiable material was removed, the arachidonic acid content of the concentrate was about 25%. These unsaturated acids were converted to their methyl esters and fractionated on a silicic acid adsorption column. The progress of the adsorption fractionation was followed by spectrophotometric examination and determination of iodine values of the eluted fractions. Methyl arachidonate of 90% purity was obtained by this means. It was further purified by fractional distillation in vacuo. The final product had an iodine value of 316.1; theory, 318.8. The purity of this preparation was further established by spectrophotometric examination, by saponification equivalents, mean molecular weight, and by x-ray diffraction patterns and melting points of a completely hydrogenated portion.Evidence of acids of greater unsaturation than arachidonic acid in suprarenal lipids was also clearly established by spectrophotometric examination. A fraction was obtained which was estimated to contain about 80–85% of a C20 acid with five double bonds. More... »

PAGES

55-58

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf02612091

DOI

http://dx.doi.org/10.1007/bf02612091

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1047562062


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/09", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Engineering", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0904", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Engineering", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Eastern Regional Research Laboratory, Philadelphia, Pennsylvania", 
          "id": "http://www.grid.ac/institutes/grid.508985.9", 
          "name": [
            "Eastern Regional Research Laboratory, Philadelphia, Pennsylvania"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Herb", 
        "givenName": "S. F.", 
        "id": "sg:person.047773421.60", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.047773421.60"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Eastern Regional Research Laboratory, Philadelphia, Pennsylvania", 
          "id": "http://www.grid.ac/institutes/grid.508985.9", 
          "name": [
            "Eastern Regional Research Laboratory, Philadelphia, Pennsylvania"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Riemenschneider", 
        "givenName": "R. W.", 
        "id": "sg:person.061134203.43", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.061134203.43"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Eastern Regional Research Laboratory, Philadelphia, Pennsylvania", 
          "id": "http://www.grid.ac/institutes/grid.508985.9", 
          "name": [
            "Eastern Regional Research Laboratory, Philadelphia, Pennsylvania"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Donaldson", 
        "givenName": "Jeanette", 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "sg:pub.10.1007/bf02651447", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1035130671", 
          "https://doi.org/10.1007/bf02651447"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "1951-02", 
    "datePublishedReg": "1951-02-01", 
    "description": "Fresh beef suprarenal glands were ground and extracted thoroughly with alcohol and then with ethyl ether. After removal of solvent the total lipid residue was saponified, and the fatty acids were recovered by extraction. The less unsaturated acids were removed by crystallization from acetone at \u221240\u00b0C. At this stage the filtrate contained essentially all the arachidonic acid originally present in the glands and also unsaponifiable matter. After the unsaponifiable material was removed, the arachidonic acid content of the concentrate was about 25%. These unsaturated acids were converted to their methyl esters and fractionated on a silicic acid adsorption column. The progress of the adsorption fractionation was followed by spectrophotometric examination and determination of iodine values of the eluted fractions. Methyl arachidonate of 90% purity was obtained by this means. It was further purified by fractional distillation in vacuo. The final product had an iodine value of 316.1; theory, 318.8. The purity of this preparation was further established by spectrophotometric examination, by saponification equivalents, mean molecular weight, and by x-ray diffraction patterns and melting points of a completely hydrogenated portion.Evidence of acids of greater unsaturation than arachidonic acid in suprarenal lipids was also clearly established by spectrophotometric examination. A fraction was obtained which was estimated to contain about 80\u201385% of a C20 acid with five double bonds.", 
    "genre": "article", 
    "id": "sg:pub.10.1007/bf02612091", 
    "inLanguage": "en", 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1082739", 
        "issn": [
          "0003-021X", 
          "1558-9331"
        ], 
        "name": "Journal of the American Oil Chemists' Society", 
        "publisher": "Wiley", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "2", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "28"
      }
    ], 
    "keywords": [
      "removal of solvent", 
      "adsorption column", 
      "ray diffraction patterns", 
      "melting point", 
      "fatty acids", 
      "unsaturated acids", 
      "arachidonic acid", 
      "adsorption fractionation", 
      "final product", 
      "diffraction patterns", 
      "C20 acids", 
      "ethyl ether", 
      "lipid residues", 
      "residues", 
      "acid", 
      "unsaponifiable material", 
      "materials", 
      "acid content", 
      "methyl ester", 
      "spectrophotometric examination", 
      "iodine value", 
      "eluted fractions", 
      "methyl arachidonate", 
      "purity", 
      "fractional distillation", 
      "distillation", 
      "molecular weight", 
      "evidence of acid", 
      "double bond", 
      "gland", 
      "ether", 
      "removal", 
      "solvent", 
      "extraction", 
      "crystallization", 
      "acetone", 
      "filtrate", 
      "unsaponifiable matter", 
      "arachidonic acid content", 
      "content", 
      "concentrate", 
      "esters", 
      "column", 
      "fractionation", 
      "values", 
      "fraction", 
      "arachidonate", 
      "vacuo", 
      "preparation", 
      "saponification equivalent", 
      "greater unsaturation", 
      "unsaturation", 
      "lipids", 
      "bonds", 
      "isolation", 
      "alcohol", 
      "stage", 
      "matter", 
      "progress", 
      "determination", 
      "means", 
      "products", 
      "theory", 
      "equivalent", 
      "weight", 
      "patterns", 
      "point", 
      "portion", 
      "evidence", 
      "examination", 
      "suprarenal gland", 
      "Fresh beef suprarenal glands", 
      "beef suprarenal glands", 
      "total lipid residue", 
      "silicic acid adsorption column", 
      "acid adsorption column", 
      "suprarenal lipids", 
      "natural arachidonic acid"
    ], 
    "name": "Isolation of natural arachidonic acid as its methyl ester", 
    "pagination": "55-58", 
    "productId": [
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1047562062"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/bf02612091"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/bf02612091", 
      "https://app.dimensions.ai/details/publication/pub.1047562062"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2021-12-01T19:39", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-springernature-scigraph/baseset/20211201/entities/gbq_results/article/article_73.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://doi.org/10.1007/bf02612091"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1007/bf02612091'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/bf02612091'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/bf02612091'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/bf02612091'


 

This table displays all metadata directly associated to this object as RDF triples.

153 TRIPLES      22 PREDICATES      105 URIs      96 LITERALS      6 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/bf02612091 schema:about anzsrc-for:09
2 anzsrc-for:0904
3 schema:author N7e9e99efafeb4de0ade484ab2127db72
4 schema:citation sg:pub.10.1007/bf02651447
5 schema:datePublished 1951-02
6 schema:datePublishedReg 1951-02-01
7 schema:description Fresh beef suprarenal glands were ground and extracted thoroughly with alcohol and then with ethyl ether. After removal of solvent the total lipid residue was saponified, and the fatty acids were recovered by extraction. The less unsaturated acids were removed by crystallization from acetone at −40°C. At this stage the filtrate contained essentially all the arachidonic acid originally present in the glands and also unsaponifiable matter. After the unsaponifiable material was removed, the arachidonic acid content of the concentrate was about 25%. These unsaturated acids were converted to their methyl esters and fractionated on a silicic acid adsorption column. The progress of the adsorption fractionation was followed by spectrophotometric examination and determination of iodine values of the eluted fractions. Methyl arachidonate of 90% purity was obtained by this means. It was further purified by fractional distillation in vacuo. The final product had an iodine value of 316.1; theory, 318.8. The purity of this preparation was further established by spectrophotometric examination, by saponification equivalents, mean molecular weight, and by x-ray diffraction patterns and melting points of a completely hydrogenated portion.Evidence of acids of greater unsaturation than arachidonic acid in suprarenal lipids was also clearly established by spectrophotometric examination. A fraction was obtained which was estimated to contain about 80–85% of a C20 acid with five double bonds.
8 schema:genre article
9 schema:inLanguage en
10 schema:isAccessibleForFree false
11 schema:isPartOf N205fc893b2264721a3afb6fabe557017
12 N66e1075b776c4bd888e986266b3b3914
13 sg:journal.1082739
14 schema:keywords C20 acids
15 Fresh beef suprarenal glands
16 acetone
17 acid
18 acid adsorption column
19 acid content
20 adsorption column
21 adsorption fractionation
22 alcohol
23 arachidonate
24 arachidonic acid
25 arachidonic acid content
26 beef suprarenal glands
27 bonds
28 column
29 concentrate
30 content
31 crystallization
32 determination
33 diffraction patterns
34 distillation
35 double bond
36 eluted fractions
37 equivalent
38 esters
39 ether
40 ethyl ether
41 evidence
42 evidence of acid
43 examination
44 extraction
45 fatty acids
46 filtrate
47 final product
48 fraction
49 fractional distillation
50 fractionation
51 gland
52 greater unsaturation
53 iodine value
54 isolation
55 lipid residues
56 lipids
57 materials
58 matter
59 means
60 melting point
61 methyl arachidonate
62 methyl ester
63 molecular weight
64 natural arachidonic acid
65 patterns
66 point
67 portion
68 preparation
69 products
70 progress
71 purity
72 ray diffraction patterns
73 removal
74 removal of solvent
75 residues
76 saponification equivalent
77 silicic acid adsorption column
78 solvent
79 spectrophotometric examination
80 stage
81 suprarenal gland
82 suprarenal lipids
83 theory
84 total lipid residue
85 unsaponifiable material
86 unsaponifiable matter
87 unsaturated acids
88 unsaturation
89 vacuo
90 values
91 weight
92 schema:name Isolation of natural arachidonic acid as its methyl ester
93 schema:pagination 55-58
94 schema:productId N8adbb8103b824301b04d519ffcc8272a
95 Naa88f136fa2649abb8dc023d14eb04ff
96 schema:sameAs https://app.dimensions.ai/details/publication/pub.1047562062
97 https://doi.org/10.1007/bf02612091
98 schema:sdDatePublished 2021-12-01T19:39
99 schema:sdLicense https://scigraph.springernature.com/explorer/license/
100 schema:sdPublisher Nb6fdacf9380c424290f75366760e05e0
101 schema:url https://doi.org/10.1007/bf02612091
102 sgo:license sg:explorer/license/
103 sgo:sdDataset articles
104 rdf:type schema:ScholarlyArticle
105 N205fc893b2264721a3afb6fabe557017 schema:volumeNumber 28
106 rdf:type schema:PublicationVolume
107 N66e1075b776c4bd888e986266b3b3914 schema:issueNumber 2
108 rdf:type schema:PublicationIssue
109 N7e9e99efafeb4de0ade484ab2127db72 rdf:first sg:person.047773421.60
110 rdf:rest N8c27aee5c09140d2bcabeaa09f3ab654
111 N8adbb8103b824301b04d519ffcc8272a schema:name doi
112 schema:value 10.1007/bf02612091
113 rdf:type schema:PropertyValue
114 N8c27aee5c09140d2bcabeaa09f3ab654 rdf:first sg:person.061134203.43
115 rdf:rest Nf07d459f53ca4b84862b205765366c37
116 Naa88f136fa2649abb8dc023d14eb04ff schema:name dimensions_id
117 schema:value pub.1047562062
118 rdf:type schema:PropertyValue
119 Nb6fdacf9380c424290f75366760e05e0 schema:name Springer Nature - SN SciGraph project
120 rdf:type schema:Organization
121 Nec4289c2a3cc427783c10aad3d76dc63 schema:affiliation grid-institutes:grid.508985.9
122 schema:familyName Donaldson
123 schema:givenName Jeanette
124 rdf:type schema:Person
125 Nf07d459f53ca4b84862b205765366c37 rdf:first Nec4289c2a3cc427783c10aad3d76dc63
126 rdf:rest rdf:nil
127 anzsrc-for:09 schema:inDefinedTermSet anzsrc-for:
128 schema:name Engineering
129 rdf:type schema:DefinedTerm
130 anzsrc-for:0904 schema:inDefinedTermSet anzsrc-for:
131 schema:name Chemical Engineering
132 rdf:type schema:DefinedTerm
133 sg:journal.1082739 schema:issn 0003-021X
134 1558-9331
135 schema:name Journal of the American Oil Chemists' Society
136 schema:publisher Wiley
137 rdf:type schema:Periodical
138 sg:person.047773421.60 schema:affiliation grid-institutes:grid.508985.9
139 schema:familyName Herb
140 schema:givenName S. F.
141 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.047773421.60
142 rdf:type schema:Person
143 sg:person.061134203.43 schema:affiliation grid-institutes:grid.508985.9
144 schema:familyName Riemenschneider
145 schema:givenName R. W.
146 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.061134203.43
147 rdf:type schema:Person
148 sg:pub.10.1007/bf02651447 schema:sameAs https://app.dimensions.ai/details/publication/pub.1035130671
149 https://doi.org/10.1007/bf02651447
150 rdf:type schema:CreativeWork
151 grid-institutes:grid.508985.9 schema:alternateName Eastern Regional Research Laboratory, Philadelphia, Pennsylvania
152 schema:name Eastern Regional Research Laboratory, Philadelphia, Pennsylvania
153 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...