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558028

Sigma-Aldrich

(S)-(+)-4-Penten-2-ol

95%

Synonym(s):

(2S)-4-Penten-2-ol, (2S)-Pent-4-en-2-ol, (S)-(+)-Pent-4-en-2-ol, (S)-(-)-Pent-4-en-2-ol, (S)-4-Penten-2-ol

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About This Item

Linear Formula:
H2C=CHCH2CH(OH)CH3
CAS Number:
55563-79-6
Molecular Weight:
86.13
MDL number:
MFCD03427200
UNSPSC Code:
12352002
PubChem Substance ID:
24879714
NACRES:
NA.22

Assay

95%

optical activity

[α]20/D +5.0°, c = 1% in chloroform

refractive index

n20/D 1.4240 (lit.)

bp

115-116 °C (lit.)

density

0.837 g/mL at 25 °C (lit.)

functional group

allyl
hydroxyl

SMILES string

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

InChI

1S/C5H10O/c1-3-4-5(2)6/h3,5-6H,1,4H2,2H3/t5-/m0/s1

InChI key

ZHZCYWWNFQUZOR-YFKPBYRVSA-N

Application

(S)-(+)-4-Penten-2-ol can be used:
  • As an intermediate in one of the key synthetic steps for the preparation of undecenolide (−)-cladospolide C.
  • To prepare a carboxamide derivative as a key intermediate for the preparation of (−)-iso-cladospolide B1.
  • To prepare S-enantiomers of hydroxyeicosa tetraenoic acid named 19-HETE.
  • To prepare an acryloyl ester derivative by reacting with acryloyl chloride, which is a key intermediate for the synthesis of parasorbic acid.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

78.0 °F - closed cup

Flash Point(C)

25.56 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN0654
MKBS6499V
MKBR2420V
MKBJ9436V
MKAA3010V

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Enantioselective total synthesis of iso-cladospolide B, cladospolide C and cladospolide B from tartaric acid
Prasad KR and Gandi VR
Tetrahedron Asymmetry, 22(5), 499-505 (2011)
A practical, stereospecific route to 18-, 19-, and 20-hydroxyeicosa-5 (Z), 8 (Z), 11 (Z), 14 (Z)-tetraenoic acids (18-, 19-, and 20-HETEs)
Gopal VR, et al.
Tetrahedron Letters, 45(12), 2563-2565 (2004)
A Chemoenzymatic Total Synthesis of the Undecenolide (−)-Cladospolide C
Banwell MG, et al.
Australian Journal of Chemistry, 58(7), 511-516 (2005)
Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions
Ramachandran PV, et al.
Tetrahedron Letters, 41(5), 583-586 (2000)

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