Absolute Configuration of a Hydroxyfuranoid Acid from the Pelage of the Genus Bos, 18-(6 S,9 R,10 R)-Bovidic Acid
Abstract
Pelage extracts of the banteng (Bos javanicus), the domestic cattle (B. taurus), the gaur (B. frontalis), and the yak (B. grunniens) were investigated by FABMS and NMR. An 18-carbon hydroxyfuranoid acid, 1 (10-hydroxy-6,9-oxidooctadecanoic acid), first reported from the wool of the domestic sheep (Ovis aries) was confirmed in B. frontalis; we suspend judgment on the occurrence of this compound in the other species we examined. The stereochemistry of 1, determined by Mosher NMR and CD tweezer methods, was assigned as 6S, 9R, 10R. We propose the name bovidic acid for this and homologous alpha-hydroxylated 2,5-tetrahydrofuranoid carboxylic acids, in reference to the family Bovidae, which represents their sole known natural source.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
The oil secreted by B. gaurus is identified as 5-(1-hydroxynonyl)-2-tetrahydrofuranpentanoic acid, named bovidic acid.
“The oil, identified as 5-(1-hydroxynonyl)-2-tetrahydrofuranpentanoic acid, has been named bovidic acid (Ishii et al. 2004), and 2 studies have found it to have mosquito repellent properties (Tran and Chauhan 2007;Phillips et al. 2015).”
From Bos frontalis and Bos gaurus (Artiodactyla: Bovidae) (2018) · cites this paper as Ishii et al. 2004
Cites
High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids
Ohtani, I. I., Kusumi, T., Kashman, Y., & Kakisawa, H. (1991) · Journal of the American Chemical Society · doi:10.1021/ja00011a006 · Cited by 3,217 · see citing works
Chemistry and Biochemistry of Natural Waxes
Arndt, K. A., & Benson, A. A. (1977) · Journal of Investigative Dermatology · doi:10.1111/1523-1747.ep12497597 · Cited by 1,208 · see citing works
(1976) · Medical Entomology and Zoology · Cited by 707 · see citing works
Nicolaides, N. (1974) · Science · doi:10.1126/science.186.4158.19 · Cited by 609 · see citing works
Sullivan, G. R., Dale, J. A., & Mosher, H. S. (1973) · The Journal of Organic Chemistry · doi:10.1021/jo00952a006 · Cited by 505 · see citing works
115th National Meeting American Chemical Society
(1949) · Chemical & Engineering News · doi:10.1021/cen-v027n009.p590 · Cited by 288 · see citing works
Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies
Huang, X., Nakanishi, K., & Berova, N. D. (2000) · Chirality · doi:10.1002/(sici)1520-636x(2000)12:4 · Cited by 269 · see citing works
Self-citationMammalian semiochemistry: the investigation of chemical signals between mammals
(1985) · Comparative Biochemistry and Physiology Part A Physiology · doi:10.1016/0300-9629(85)90947-8 · Cited by 188 · see citing works
Baldwin, J. E., & Johnson, D. S. (1973) · The Journal of Organic Chemistry · doi:10.1021/jo00952a007 · Cited by 35 · see citing works
Allylic Rearrangements. XXXIV. The Reaction of Trimethylamine with α-Methylallyl Chloride1a,b
Young, W. G., Clement, R. A., & Shih, C.-H. (1955) · Journal of the American Chemical Society · doi:10.1021/ja01616a039 · Cited by 12 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Bos frontalis and Bos gaurus (Artiodactyla: Bovidae)
Ahrestani, F. S. (2018) · Mammalian Species · doi:10.1093/mspecies/sey004 · Cited by 26 · see citing works
Phillips, G. A., Wright, T. B., Stevens, A. C., & Pagenkopf, B. L. (2015) · Canadian Journal of Chemistry · doi:10.1139/cjc-2014-0288 · Cited by 8 · see citing works
- Authors
- Ishii, H., Krane, S., Itagaki, Y., Berova, N., Nakanishi, K., & Weldon, P. J.
- Affiliations
- Wildlife Conservation Society (US)
- Corresponding author
- Nakanishi, Koji
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-07-31
- Volume
- 67
- Issue
- 8
- Pages
- 1426-1430
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W2044941375
- Cited by
- 35
- References
- 11
- Citations by year
- 2025: 1 · 2023: 1 · 2022: 4 · 2021: 3 · 2020: 4 · 2018: 1 · 2017: 1 · 2016: 1 · 2015: 1 · 2014: 2 · 2012: 3
- FWCI
- 0.96
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institute of General Medical Sciences (GM34509)
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Plant chemical constituents analysis
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Plant Surface Properties and Treatments
- Keywords
- absolute configuration, fur, Bos javanicus, cattle, Bos frontalis, yak, gaur, banteng, stereochemistry, natural products
- MeSH terms
- Animals, Cattle, Circular Dichroism, Hair, Sheep, Stearic Acids, Stereoisomerism, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
