alpha-Pinene, (+)-

HCID 82227
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
7785-70-8
Standard SMILES
CC1=CC[C@@H]2C[C@H]1C2(C)C
InChIKey
GRWFGVWFFZKLTI-RKDXNWHRSA-N
Molecular formula
C10H16
Average molar mass
136.23 g/mol
Monoisotopic mass
136.12520051

Overview

(+)-alpha-pinene is the (+)-enantiomer of alpha-pinene. It has a role as a plant metabolite and a human metabolite. It is an enantiomer of a (-)-alpha-pinene.

Names & identifiers

Preferred name
alpha-Pinene, (+)-
IUPAC
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
English name
(1R)-(+)-alpha-Pinene
Molecular formula
C10H16
Molecular weight
136.23

Names & synonyms

(+)-alpha-Pinene7785-70-8(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene(1R)-(+)-alpha-Pinene(+)-2-Pinenealpha-Pinene, (+)-d-.alpha.-Pinenealpha-Pinene(dextro)(1R)-alpha-Pinene(+)-Pin-2(3)-ene(+)-.alpha.-PineneDTXSID7041671
Show more names
(1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene(+)-α-PineneFEMA 2902(1R)-(+)-α-pinene(+)-a-pineneα-Pinene dextro(1R,5R)-2-6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-2-ENE(1R)-(+)-a-pineneAlpha Pinene Dextro2,6,6-trimethyl-,(1R)-Bicyclo[3.1.1]hept-2-ene
H6CM4TWH1W(1R,5R)-pin-2-eneBicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1R,5R)-CCRIS 9059EINECS 232-087-8.ALPHA.-PINENE, D-(+)-3,6,6-TRIMETHYLBICYCLO[3.1.1]HEPT-2-ENE.ALPHA.-PINENE-(+)

Database identifiers

CAS
7785-70-8
PubChem CID
82227
DTXSID
DTXSID7041671
ChEMBL
CHEMBL1236329
ChEBI
CHEBI:28261
UNII
H6CM4TWH1W
EC Number
232-087-8
Nikkaji
J95.399G

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Terpenes
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
FragrancesFragrance Ingredient (d-.alpha.-Pinene) -> IFRA transparency List
LogP4.44
Density0.855-0.860
Solubility · 2 items

Insoluble in water; soluble in oils

Soluble (in ethanol)

Physicochemical properties

Melting point
62 °C · −62 °C(lit.)
Boiling point
155 · 155-156 °C(lit.)
Density
0.858 g/mL · 0.858 g/mL at 20 °C(lit.)
vapor pressure
5 hPa · 5 hPa (25 °C)
FEMA
2902 · 2902 | ALPHA-PINENE
refractive index
20 · n20/D 1.465(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.3% (5 of 1465) of reports.

Danger

H226 (99.7%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P321, P331, P332+P317, P333+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1465 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 4 items

Chemical: Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1R)-

Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1R,5R)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1R,5R)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 18-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/9984

(1R)-(+)-a-pinene: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Alpha-pinene: Human health tier II assessment
Hazards SummaryA skin and strong eye irritant; May cause allergic reactions in sensitive individuals, based on QSAR modeling; [Sigma-Aldrich MSDS] See alpha-Pinene.
Hazard Classes and Categories · 2 items

Flam. Liq. 3 (99.7%)

Acute toxicity (ingestion) - category 4

Toxicology

Adverse EffectsNeurotoxin - Acute solvent syndrome

Safety data

F
10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
DT7000000
ridadr
UN 2368 3/PG 3

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

U.S. Production2023: 10,000,000 - <50,000,000 lb
Industry UsesIntermediates
Household ProductsInformation on 2 consumer products that contain D-Alpha-Pinene in the following categories is provided:
Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1R,5R)-: ACTIVE

Applications · 4 items

Uses(1R)-(+)-α-Pinene is used in hydroboration reactions and the reduction of ketones.

Uses(+)-alpha-Pinene is employed in the preparation of chiral hydroboration reagents. It is a bronchodilator in humans. α-Pinene is an anti-inflammatory and used as a broad-spectrum antibiotic.It exhibits activity as an acetylcholinesterase inhibitor, aiding memory. It is a biosynthetic base for CB2 ligands, such as HU-308.

Uses(+)-α-Pinene has been used in a tolerance testing procedure to detect the genes in Marinobacter aquaeolei, for engineering a pinene tolerant Escherichia coli.

General Description(+)-α-Pinene is a monoterpenoid compound mainly found in Pinus species.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Additional notes

DefinitionChEBI: The (+)-enantiomer of alpha-pinene.

Related reactions

6 records
New reaction record

Compound notes

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