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40577

Sigma-Aldrich

(S)-1-Octen-3-ol

≥95% (sum of enantiomers, GC)

Synonym(s):

(S)-Matsutake alcohol

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About This Item

Empirical Formula (Hill Notation):
C8H16O
CAS Number:
24587-53-9
Molecular Weight:
128.21
MDL number:
MFCD04972323
UNSPSC Code:
12352002
PubChem Substance ID:
57650004
NACRES:
NA.22

Assay

≥95% (sum of enantiomers, GC)

form

liquid

optical purity

enantiomeric ratio: ≥99:1 (GC)

SMILES string

CCCCC[C@H](O)C=C

InChI

1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3/t8-/m1/s1

InChI key

VSMOENVRRABVKN-MRVPVSSYSA-N

Application

(S)-1-Octen-3-ol can be used:
  • As an odorant in the study of an olfactory sensory map of the Anopheles gambiae maxillary palp.
  • As an intermediate in the synthesis of natural product polyporolide and a prostaglandin named 8-aza-prostaglandin E1.
  • As a substrate in the preparation of trienols by reacting with 1-iodo-1,3-dienes using Pd(OAc)2/AgOAc.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

154.4 °F - closed cup

Flash Point(C)

68 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A stereoselective synthesis of the reported structure of polyporolide
Patil PH and Fernandes RA
Royal Society of Chemistry Advances, 5(61), 49189-49194 (2015)
Odor coding in the maxillary palp of the malaria vector mosquito Anopheles gambiae
Lu T, et al.
Current Biology, 17(18), 1533-1544 (2007)
Jonathan D Bohbot et al.
PloS one, 4(9), e7032-e7032 (2009-09-16)
Enantiomers differ only in the left or right handedness (chirality) of their orientations and exhibit identical chemical and physical properties. In chemical communication systems, enantiomers can be differentially active at the physiological and behavioral levels. Only recently were enantioselective odorant
Damien Brandt et al.
Organic letters, 14(21), 5594-5597 (2012-10-24)
The stereoselective synthesis of conjugated trienes has been achieved from allylic alcohols and 1-iodo-1,3-dienes using Pd(OAc)(2)/AgOAc.
Alan J Grant et al.
PloS one, 6(6), e21785-e21785 (2011-07-09)
1-Octen-3-ol (octenol) is a common attractant released by vertebrates which in combination with carbon dioxide (CO(2)) attracts hematophagous arthropods including mosquitoes. A receptor neuron contained within basiconic sensilla on the maxillary palps of adult mosquitoes responds selectively to 1-octen-3-ol. Recently
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