ISOPRENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H8
Molecular Weight	68.117
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=C)C=C

InChI

InChIKey=RRHGJUQNOFWUDK-UHFFFAOYSA-N

InChI=1S/C5H8/c1-4-5(2)3/h4H,1-2H2,3H3

HIDE SMILES / InChI

Molecular Formula	C5H8
Molecular Weight	68.117
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Relationship of isopentenyl diphosphate (IDP) isomerase activity to isoprene emission of oak leaves.	2002-10	12359528
In-situ chemical analyses of trans-polyisoprene by histochemical staining and Fourier transform infrared microspectroscopy in a rubber-producing plant, Eucommia ulmoides Oliver.	2002-10	12355153
On-line analysis of the (13)CO(2) labeling of leaf isoprene suggests multiple subcellular origins of isoprene precursors.	2002-10	12355149
The HMG-CoA reductase inhibitor lovastatin protects cells from the antineoplastic drugs doxorubicin and etoposide.	2002-10	12239596
Ubiquinol inhibition of neutral sphingomyelinase in liver plasma membrane: specific inhibition of the Mg(2+)-dependent enzyme and role of isoprenoid chain.	2002-09-27	12270134
Isolation and structure of [HC[CH(SiMe(3))(SnMe(3))](2)](+): a remarkably stable sec-alkyl cation.	2002-09-25	12236730
Synthesis of 7-substituted farnesyl diphosphate analogues.	2002-09-05	12201708
Isoprenoid biosynthesis in higher plants and in Escherichia coli: on the branching in the methylerythritol phosphate pathway and the independent biosynthesis of isopentenyl diphosphate and dimethylallyl diphosphate.	2002-09-01	12010124
Pseudonocardia spinosispora sp. nov., isolated from Korean soil.	2002-09	12361262
Reversal of P-glycoprotein-mediated paclitaxel resistance by new synthetic isoprenoids in human bladder cancer cell line.	2002-09	12359058
Hydroxy peroxy nitrites and nitrates from OH initiated reactions of isoprene.	2002-08-14	12167055
Mevalonate and nonmevalonate pathways for the biosynthesis of isoprene units.	2002-08	12353619
Allergens and natural rubber proteins.	2002-08	12170241
Photoaffinity analogues of farnesyl pyrophosphate transferable by protein farnesyl transferase.	2002-07-17	12105898
Breath biomarkers for detection of human liver diseases: preliminary study.	2002-07-10	12101636
Attraction of the tropical bont tick, Amblyomma variegatum, to human breath and to the breath components acetone, NO and CO2.	2002-07	12216862
Gordonia westfalica sp. nov., a novel rubber-degrading actinomycete.	2002-07	12148617
Upper airway and pulmonary effects of oxidation products of (+)-alpha-pinene, d-limonene, and isoprene in BALB/c mice.	2002-07	12122569
Differential accumulation of dimethylallyl diphosphate in leaves and needles of isoprene- and methylbutenol-emitting and nonemitting species.	2002-07	12114581
Characterisation of NMHCs in a French urban atmosphere: overview of the main sources.	2002-06-26	12146518
Construction and intergeneric conjugative transfer of a pSG5-based cosmid vector from Escherichia coli to the polyisoprene rubber degrading strain Micromonospora aurantiaca W2b.	2002-06-04	12076802
Breath markers and soluble lipid peroxidation markers in critically ill patients.	2002-06	12211653
Metabolic and environmental regulation of 3-methylcrotonyl-coenzyme A carboxylase expression in Arabidopsis.	2002-06	12068107
Origin of two isoprenoid units in a lavandulyl moiety of sophoraflavanone G from Sophora flavescens cultured cells.	2002-06	12031444
Isoprene synthase activity parallels fluctuations of isoprene release during growth of Bacillus subtilis.	2002-05-31	12054742
TMS triflate-catalyzed cleavage of prenyl (3-methylbut-2-enyl) ester.	2002-05-30	12027654
Aromatic farnesyl diphosphate analogues: vinyl triflate-mediated synthesis and preliminary enzymatic evaluation.	2002-05-20	11992789
Protection by isoprene against singlet oxygen in leaves.	2002-05	12011357
Polyene substrates with unusual methylation patterns to probe the active sites of three catalytic antibodies.	2002-05	11886788
Volatile metabolites from actinomycetes.	2002-04-24	11958631
Optimization of a mist chamber (Cofer scrubber) for sampling water-soluble organics in air.	2002-04-15	11993879
Lack of isoprene overproduction during peritoneal dialysis.	2002-04-04	11929143
Performance characteristics and applications of a proton transfer reaction-mass spectrometer for measuring volatile organic compounds in ambient air.	2002-04-01	11999066
[Phytogenic isoprene and its ecological significance].	2002-04	12222064
Reptilian chemistry: volatile compounds from paracloacal glands of the American crocodile (Crocodylus acutus).	2002-04	12035925
Mechanism of OH formation from ozonolysis of isoprene: a quantum-chemical study.	2002-03-20	11890820
HPLC-MS determination of the oxidation products of the reaction between alpha- and beta-pinene and OH radicals.	2002-03	11941431
Incorporation of [1-(13)C]1-deoxy-D-xylulose into isoprenoids of the liverwort Conocephalum conicum.	2002-02	11830134
Volatile isoprenoid constituents of fruits, vegetables and herbs cumulatively suppress the proliferation of murine B16 melanoma and human HL-60 leukemia cells.	2002-01-25	11741740
[Overlooked targets for the development of antibacterial and antimalarial drugs and herbicides: diverse biosynthetic systems for the isoprene units].	2002-01	11808197
Identification of mammary carcinogens in rodent bioassays.	2002	11921183
Tobacco smoke carcinogens and breast cancer.	2002	11921179
Taxonomic characterization of two rubber degrading bacteria belonging to the species Gordonia polyisoprenivorans and analysis of hyper variable regions of 16S rDNA sequences.	2001-12-18	11750816
Isoprene produced by leaves protects the photosynthetic apparatus against ozone damage, quenches ozone products, and reduces lipid peroxidation of cellular membranes.	2001-12	11743121
Zeaxanthin and menaquinone-7 biosynthesis in Sphingobacterium multivorum via the methylerythritol phosphate pathway.	2001-11-13	11731147
Diene-Containing half-sandwich MoIII complexes as ethylene polymerization catalysts: experimental and theoretical studies.	2001-11-05	11757648
[Development of biogenic VOC emissions inventory with high temporal and spatial resolution].	2001-11	11855173
Isoprenoid biosynthesis via 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol 4-phosphate (DOXP/MEP) pathway.	2001	11833775
Modelling the responses to biological reactive intermediates: establishing the borderlines of risk.	2001	11764997
Bacterial degradation of natural and synthetic rubber.	2001	11749186

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:11:54 GMT 2025` Edited by `admin` on `Mon Mar 31 19:11:54 GMT 2025`
Record UNII	0A62964IBU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-9237

Preferred Name

English

ISOPRENE

Systematic Name

English

2-METHYL-1,3-BUTADIENE

Systematic Name

English

ISOPRENE [IARC]

Common Name

English

2-METHYLBUTADIENE

Systematic Name

English

.BETA.-METHYLBIVINYL

Common Name

English

ISOPENTADIENE

Systematic Name

English

ISOPRENE [HSDB]

Common Name

English

ISOPRENE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C44351